Condensed heterocyclic derivatives and herbicides

ABSTRACT

A condensed heterocyclic derivative of the formula (I): ##STR1## (wherein R is a hydroxyl group, R 3  or R 4  is an alkoxy group, W is an oxygen atom, Yn is a hydrogen atom, Z is a methine group, and A is a 5- or 6-membered heterocyclic ring which may be substituted, and a herbicide, are presented. When used for paddy field treatment, upland soil treatment and foliage treatment, the condensed heterocyclic derivative of the present invention exhibits excellent herbicidal activities against gramineous and non-gramineous weeds without adversely affecting crop plants.

TECHNICAL FIELD

The present invention relates to condensed heterocyclic derivatives and their salts as well as herbicides containing them as active ingredients, which can be applied to paddy fields, upland fields and non-agricultural fields.

BACKGROUND ART

The present inventors found that quinoline and naphthalene derivatives have herbicidal activities and disclosed specific examples in Japanese Unexamined Patent Publication No. 56469/1990. Further, Japanese Unexamined Patent Publication No. 121973/1990 discloses that aromatic carboxylic acid derivatives containing quinoline, naphthalene, benzofuran, thiophene or pyridine ring have herbicidal activities.

However, the above-mentioned publications disclose nothing about specific compounds relating to the condensed heterocyclic derivatives of the present invention. Further, these compounds are not necessarily satisfactory from the viewpoint of the herbicidal effects. A number of other herbicides have been developed and contributed to the saving of energy for agricultural operations and to the improvement of the productivity. However, in their practical use, such herbicides also have various problems with respect to the herbicidal effects and the safety to crop plants.

The present inventors have conducted an extensive research on condensed heterocyclic derivatives with an object to develop a compound which is excellent in the herbicidal activities without bringing about phytotoxicity to crop plants. As a result, it has been found that the compounds of the present invention which are pyrimidine or triazine derivatives bonded to a condensed heterocyclic ring exhibit excellent herbicidal activities against not only annual weeds but also perennial gramineous weeds, cyperaceous weeds and broad leaf weeds in the paddy field treatment, upland soil treatment and foliage treatment, and they are highly safe to crop plants. The present invention has been accomplished on the basis of this discovery.

DISCLOSURE OF THE INVENTION

Namely, the present invention relates to a condensed heterocyclic derivative of the formula (I): ##STR2## {wherein A is a heterocyclic ring of the formula ##STR3## R is a hydrogen atom, a hydroxyl group, an alkoxy group which may be substituted, a benzyloxy group which may be substituted, an aryloxy group which may be substituted, an alkylthio group which may be substituted, a benzylthio group which may be substituted, an arylthio group which may be substituted, an alkenyloxy group which may be substituted, an alkynyloxy group which may be substituted, an alkenylthio group which may be substituted, an alkynylthio group which may be substituted, an alkylideneaminoxy group, or a group of the formula --NR⁶ R⁷ (wherein each of R⁶ and R⁷ which may be the same or different, is a hydrogen atom, an alkyl group, an alkoxy group, a benzyl group, an aryl group which may be substituted, an alkylsulfonyl group, or an arylsulfonyl group which may be substituted, or R⁶ and R⁷ may, together with the nitrogen atom, form a ring which may contain a hetero atom), each of R¹ and R² which may be the same or different, is a hydrogen atom, a formyl group, an alkylcarbonyl group which may be substituted, a cycloalkylcarbonyl group, an arylcarbonyl group which may be substituted, a pyridylcarbonyl group which may be substituted, a carboxyl group, a group of the formula --CONR⁶ R⁷ (wherein R⁶ and R⁷ are as defined above), an alkylthiocarbonyl group which may be substituted, a cycloalkylthiocarbonyl group, an aryloxycarbonyl group which may be substituted, an alkoxycarbonyl group which may be substituted, a cycloalkyl group, an alkyl group which may be substituted, an alkenyl group which may be substituted, an alkynyl group which may be substituted, an alkoxy group which may be substituted, an aryl group which may be substituted, a halogen atom, a benzyloxycarbonyl group which may be substituted, a benzylthiocarbonyl group which may be substituted, a cycloalkoxycarbonyl group, an arylthiocarbonyl group which may be substituted, an alkenyloxycarbonyl group which may be substituted, an alkynyloxycarbonyl group which may be substituted, an alkenylthiocarbonyl group which may be substituted, an alkynylthiocarbonyl group which may be substituted, an isopropylideneaminoxycarbonyl group, a nitro group, a cyano group, a halogenated carbonyl group, a group of the formula CR⁸ ═N--R⁹ (wherein R⁸ is a hydrogen atom, an aryl group, or an alkyl group, and R⁹ is a hydroxyl group, an alkyl group, an aryl group which may be substituted, a benzyl group which may be substituted, a benzyloxy group which may be substituted, an alkoxy group, an alkenyloxy group, an alkynyloxy group, a phenoxy group which may be substituted, an alkylamino group, a dialkylamino group, an arylamino group which may be substituted, or an arylsulfonylamino group which may be substituted), a group of the formula NR¹⁰ R¹¹ (wherein each of R¹⁰ and R¹¹ which may be the same or different, is a hydrogen atom, an alkyl group, an aryl group which may be substituted, a benzyl group which may be substituted, a formyl group, an alkylcarbonyl group which may be substituted, a cycloalkylcarbonyl group, an arylcarbonyl group which may be substituted, a pyridylcarbonyl group which may be substituted, an alkoxycarbonyl group, an alkylsulfonyl group, an arylsulfonyl group which may be substituted, a carbamoyl group, an alkylthiocarbonyl group or an arylthiocarbonyl group which may be substituted, or R¹⁰ and R¹¹ may, together with the nitrogen atom, form a ring which may contain a hetero atom), a group of the formula N═CR¹² R¹³ (wherein each of R¹² and R¹³ which may be the same or different, is a hydrogen atom, an alkyl group, or an aryl group which may be substituted, or R¹² and R¹³ may form a ring which may contain a hetero atom), each of R³ and R⁴ which may be the same or different, is a hydrogen atom, an alkoxy group which may be substituted, a halogen atom, an alkylamino group, a dialkylamino group, or an alkyl group which may be substituted, R⁵ is a hydrogen atom, an alkyl group which may be substituted, a formyl group, an alkylcarbonyl group which may be substituted, a cycloalkylcarbonyl group, an arylcarbonyl group which may be substituted, a pyridylcarbonyl group which may be substituted, a carbamoyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a benzyloxycarbonyl group, an alkylthiocarbonyl group, an arylthiocarbonyl group, an alkylsulfonyl group, an arylsulfonyl group, a trialkylsilyl group, an alkenyl group, an alkynyl group, a 4,6-dimethoxypyridin-2-yl group, or trichloromethylthio group, each of X¹ and X² which may be the same or different, is an oxygen atom, a sulfur atom, a methylene group, a group of the formula NR¹⁴ (wherein R¹⁴ is a hydrogen atom or an alkyl group), a carbonyl group, a group of the formula C═NOR¹⁵ (wherein R¹⁵ is an alkyl group), or a hydroxymethylene group, Q¹ is a methylene group, a carbonyl group, or a group of the formula C═C<R¹⁶ R¹⁷ (wherein each of R¹⁶ and R¹⁷ which may be the same or different, is a cyano group, a cycloalkylcarbonyl group, a benzoyl group, or an alkoxycarbonyl group), each of Q² and Q³ which may be the same or different is a group of the formula C<R¹⁸ R¹⁹ [wherein each of R¹⁸ and R¹⁹ which may be the same or different, is a hydrogen atom, an alkyl group, or an alkoxycarbonyl group, or R¹⁸ and R¹⁹ together form a carbonyl group or a group of the formula C═CHR²⁰ (wherein R²⁰ is a hydrogen atom or an alkyl group)], and each of a, b, d and e is a nitrogen atom or a methine group, provided that at least one of them is a nitrogen atom (provided that a case where each of a, b and d is a methine group and e is a nitrogen atom, and the formula (I) represents a 8-quinolinecarboxylic acid derivative, is excluded), Y is a halogen atom, an alkyl group which may be substituted, an alkoxy group, a phenyl group which may be substituted, a nitro group, an alkylamino group, or a dialkylamino group, n is an integer of from 0 to 2, provided that when n is 2, it may represent a combination of different groups, W is an oxygen atom, a sulfur atom, an N-formyl group, a methylene group, a carbonyl group, a cyanomethylene group, and Z is a methine group or a nitrogen atom}, or its salt; and a herbicide containing it as an active ingredient.

As preferred compounds, among them, those of the formula (I) wherein R is a hydrogen atom, a hydroxyl group and a C₁ -C₆ alkoxy group, may, for example, be mentioned. R³ and R⁴ may, for example, be a halogen atom, which may be a chlorine, bromine, fluorine or iodine atom, a C₁ -C₆ alkyl group or an alkoxy group.

Further, R¹ and R² may, for example, be a C₁ -C₈ alkyl group, a formyl group, a C₁ -C₈ alkylcarbonyl group, a C₁ -C₈ alkoxycarbonyl group, a C₁ -C₈ alkylthiocarbonyl group, C₃ -C₈ cycloalkoxycarbonyl group, a C₃ -C₈ cycloalkylthiocarbony group, a C₃ -C₆ alkenyloxycarbonyl group which may be substituted, a C₃ -C₆ alkenylthiocarbonyl group, a C₃ -C₆ alkynyloxycarbonyl group which may be substituted, or a C₃ -C₆ alkynylthiocarbonyl group, and R⁵ may, for example, be a hydrogen atom, a formyl group, or a C₁ -C₈ alkylcarbonyl group. Now, specific examples of the compound of the present invention will be shown in Tables 1 to 59. The compound numbers will be referred to in the subsequent description.

                                      TABLE 1                                      __________________________________________________________________________      ##STR4##                                                                      Compound                            m.p. (°C.)                          No.   R.sup.1                                                                           R.sup.2                                                                              R           W X Yn                                                                               Z  or (n.sub.D.sup.20)                        __________________________________________________________________________     1     CH.sub.3                                                                          COOC.sub.2 H.sub.5                                                                    ##STR5##   O O H CH 127-131                                    2     CH.sub.3                                                                          COOC.sub.2 H.sub.5                                                                   OH          O O H CH 160-163                                    3     CH.sub.3                                                                          COOC.sub.2 H.sub.5                                                                   OCH.sub.3   O O H CH 132-133.5                                  4     CH.sub.3                                                                          COOC.sub.2 H.sub.5                                                                    ##STR6##   O O H CH 92-93                                      5     CH.sub.3                                                                          COOC.sub.2 H.sub.5                                                                   NHSO.sub.2 CH.sub.3                                                                        O O H CH                                            6     CH.sub.3                                                                          COOC.sub.2 H.sub.5                                                                   OCH.sub.2 COOC.sub.2 H.sub.5                                                               O O H CH 92-94.5                                    7     CH.sub.3                                                                          COOC.sub.2 H.sub.5                                                                   OC.sub.2 H.sub.5                                                                           O O H CH 130-131                                    8     CH.sub.3                                                                          COOC.sub.2 H.sub.5                                                                    ##STR7##   O O H CH 106.5-109                                  9     CH.sub.3                                                                          COOC.sub.2 H.sub.5                                                                    ##STR8##   O O H CH 153-157                                    10    CH.sub.3                                                                          COOC.sub.2 H.sub.5                                                                    ##STR9##   O O H CH 130.5-132                                  11    CH.sub.3                                                                          COOC.sub.2 H.sub.5                                                                    ##STR10##  O O H CH 112.5-114                                  12    CH.sub.3                                                                          COOC.sub.2 H.sub.5                                                                   OCH.sub.2 OC.sub.2 H.sub.5                                                                 O O H CH 113-116                                    13    CH.sub.3                                                                          COOC.sub.2 H.sub.5                                                                    ##STR11##  O O H CH 1.5429                                     14    CH.sub.3                                                                          COOC.sub.2 H.sub.5                                                                   OC.sub.3 H.sub.7                                                                           O O H CH 119-121                                    15    CH.sub.3                                                                          COOC.sub.2 H.sub.5                                                                   OC.sub.3 H.sub.7 -i                                                                        O O H CH 88.5-90                                    __________________________________________________________________________

                                      TABLE 2                                      __________________________________________________________________________     Compound                             m.p. (°C.)                         No.   R.sup.1                                                                           R.sup.2  R         W X Yn                                                                               Z  or (n.sub.D.sup.20)                       __________________________________________________________________________     16    CH.sub.3                                                                          COOC.sub.2 H.sub.5                                                                       ##STR12##                                                                               O O H CH 146-148                                   17    CH.sub.3                                                                          COOC.sub.2 H.sub.5                                                                       ##STR13##                                                                               S O H CH                                           18    CH.sub.3                                                                          COOC.sub.2 H.sub.5                                                                      OH        S O H CH                                           19    CH.sub.3                                                                          COOC.sub.2 H.sub.5                                                                       ##STR14##                                                                               S O H CH                                           20    CH.sub.3                                                                          COOC.sub.2 H.sub.4 C.sub.3 H.sub.7 -i                                                    ##STR15##                                                                               O O H CH 141-144                                   21    CH.sub.3                                                                          COOC.sub.2 H.sub.4 C.sub.3 H.sub.7 -i                                                   OH        O O H CH 140.5-143                                 22    CH.sub.3                                                                          COOC.sub.2 H.sub.4 C.sub.3 H.sub.7 -i                                                    ##STR16##                                                                               O O H CH 1.5310                                    23    CH.sub.3                                                                          COOCH.sub.3                                                                              ##STR17##                                                                               O O H CH 1.5839                                    24    CH.sub.3                                                                          COOCH.sub.3                                                                             OH        O O H CH 174-178                                   25    CH.sub.3                                                                          COOCH.sub.3                                                                             OCH.sub.3 O O H CH                                           26    CH.sub.3                                                                          COOCH.sub.3                                                                              ##STR18##                                                                               O O H CH 126-130                                   27    CH.sub.3                                                                          COOCH.sub.3                                                                             OH        S O H CH 219-223                                   28    CH.sub.3                                                                          COOCH.sub.3                                                                              ##STR19##                                                                               S O H CH                                           29    CH.sub.3                                                                          COOCH.sub.3                                                                              ##STR20##                                                                               S O H CH                                           30    CH.sub.3                                                                          COOCH.sub.3                                                                             OH        O O H N  182-185                                   __________________________________________________________________________

                                      TABLE 3                                      __________________________________________________________________________     Compound                            m.p. (°C.)                          No.   R.sup.1                                                                           R.sup.2 R         W X Yn                                                                               Z  or (n.sub.D.sup.20)                        __________________________________________________________________________     31    CH.sub.3                                                                          COOCH.sub.3                                                                             ##STR21##                                                                               O O H N  88-90                                      32    CH.sub.3                                                                          COOCH.sub.3                                                                             ##STR22##                                                                               O O H N  120-122                                    33    CH.sub.3                                                                          COOCH.sub.3                                                                            OH        S O H N                                             34    CH.sub.3                                                                          COOC.sub.3 H.sub.7                                                                     OH        O O H CH 162-166                                    35    CH.sub.3                                                                          COOC.sub.4 H.sub.9 -s                                                                  OH        O O H CH 144-147.5                                  36    CH.sub.3                                                                          COOC.sub.4 H.sub.9                                                                     OH        O O H CH 160-164                                    37    CH.sub.3                                                                          CONH.sub.2                                                                             OH        O O H CH                                            38    CH.sub.3                                                                          COOH    OH        O O H CH 186-188                                    39    CH.sub.3                                                                          COCH.sub.3                                                                              ##STR23##                                                                               O O H CH 62-65                                      40    CH.sub.3                                                                          COCH.sub.3                                                                             OH        O O H CH 166-169                                    41    CH.sub.3                                                                          COCH.sub.3                                                                             OCH.sub.3 O O H CH 178-181                                    42    CH.sub.3                                                                          COCH.sub.3                                                                              ##STR24##                                                                               O O H CH 122-125                                    43    CH.sub.3                                                                          COCH.sub.3                                                                             NHSO.sub.2 CH.sub.3                                                                      O O H CH                                            44    CH.sub.3                                                                           ##STR25##                                                                             OCH.sub.3 O O H CH 101-103                                    45    CH.sub.3                                                                           ##STR26##                                                                              ##STR27##                                                                               O O H CH 1.5778                                     46    CH.sub.3                                                                           ##STR28##                                                                             OH        O O H CH                                            47    CH.sub.3                                                                           ##STR29##                                                                              ##STR30##                                                                               O O H CH 120-123                                    48    CH.sub.3                                                                           ##STR31##                                                                             OH        O O H CH 184-187                                    __________________________________________________________________________

                                      TABLE 4                                      __________________________________________________________________________     Compound                                 m.p. (°C.)                     No.   R.sup.1                                                                           R.sup.2       R        W X Yn                                                                               Z  or (n.sub.D.sup.20)                   __________________________________________________________________________     49    CH.sub.3                                                                           ##STR32##    OCH.sub.3                                                                               O O H CH 169-172                               50    CH.sub.3                                                                           ##STR33##                                                                                    ##STR34##                                                                              O O H CH 115-117                               51    CH.sub.3                                                                           ##STR35##    OCH.sub.3                                                                               O O H CH 133-137                               52    CH.sub.3                                                                           ##STR36##    OCH.sub.2 OC.sub.2 H.sub.5                                                              O O H CH 127-130                               53    CH.sub.3                                                                           ##STR37##    OCH.sub.3                                                                               O O H CH 168-170.5                             54    CH.sub.3                                                                           ##STR38##    OH       O O H CH                                       55    CH.sub.3                                                                           ##STR39##    OCH.sub.3                                                                               O O H CH 128-131                               56    CH.sub.3                                                                           ##STR40##    OH       O O H CH                                       57    CH.sub.3                                                                           ##STR41##    OCH.sub.3                                                                               O O H CH 170--173.5                            58    CH.sub.3                                                                           ##STR42##    OH       O O H CH                                       59    CH.sub.3                                                                          COC.sub.4 H.sub.9 -i                                                                         OH       O O H CH 168-171                               60    CH.sub.3                                                                          CN            OH       O O H CH 175-179                               __________________________________________________________________________

                                      TABLE 5                                      __________________________________________________________________________     Compound                             m.p. (°C.)                         No.   R.sup.1                                                                           R.sup.2  R         W X Yn                                                                               Z  or (n.sub.D.sup.20)                       __________________________________________________________________________     61    H  COOC.sub.2 H.sub.5                                                                      OH        O O H CH 161-163                                   62    H  COOC.sub.2 H.sub.5                                                                       ##STR43##                                                                               O O H CH 1.5351                                    63    H  COOC.sub.2 H.sub.5                                                                       ##STR44##                                                                               O O H CH 91.5-93                                   64    H  CN       OH        O O H CH                                           65    H  CN                                                                                       ##STR45##                                                                               O O H CH                                           66    H  CN                                                                                       ##STR46##                                                                               O O H CH                                           67    CF.sub.3                                                                          COOCH.sub.3                                                                             OH        O O H CH                                           68    CH.sub.3                                                                          COC.sub.4 H.sub.9 -i                                                                     ##STR47##                                                                               O O H CH 1.5765                                    69    CF.sub.3                                                                           ##STR48##                                                                              OCH.sub.3 O O H CH 155-158                                   70    CF.sub.3                                                                           ##STR49##                                                                              OH        O O H CH 178-181                                   71    C.sub.2 H.sub.5                                                                   COOC.sub.2 H.sub.5                                                                      OH        O O H CH 159.5-162                                 72    C.sub.2 H.sub.5                                                                   COOC.sub.2 H.sub.5                                                                       ##STR50##                                                                               O O H CH 116-120                                   73    C.sub.2 H.sub.5                                                                   COOC.sub.2 H.sub.5                                                                       ##STR51##                                                                               O O H CH 1.5339                                    74    C.sub.2 H.sub.5                                                                   COOC.sub.3 H.sub.7                                                                      OH        O O H CH 119-122                                   __________________________________________________________________________

                                      TABLE 6                                      __________________________________________________________________________     Compound                                m.p. (°C.)                      No.   R.sup.1                                                                              R.sup.2  R         W X Yn                                                                               Z  or (n.sub.D.sup.20)                    __________________________________________________________________________     75    C.sub.2 H.sub.5                                                                      COOC.sub.3 H.sub.7                                                                       ##STR52##                                                                               O O H CH 108-109.5                              76    C.sub.2 H.sub.5                                                                      COOC.sub.3 H.sub.7 -i                                                                   OH        O O H CH 137-140                                77    CF.sub.3                                                                              ##STR53##                                                                              O.sup.-  Na.sup.+                                                                        O O H CH >300                                   78    CF.sub.3                                                                              ##STR54##                                                                               ##STR55##                                                                               O O H CH 143-146                                79    CH.sub.2 Cl                                                                          COOC.sub.2 H.sub.5                                                                      OH        O O H CH                                        80    C.sub.2 H.sub.5                                                                      COOC.sub.3 H.sub.7 -i                                                                    ##STR56##                                                                               O O H CH 94-96                                  81    CH.sub.2 Cl                                                                          COOC.sub.2 H.sub.5                                                                       ##STR57##                                                                               O O H CH                                        82                                                                                    ##STR58##                                                                           COCH.sub.3                                                                              OCH.sub.3 O O H CH 151-154.5                              83                                                                                    ##STR59##                                                                           COCH.sub.3                                                                              OH        O O H CH                                        84                                                                                    ##STR60##                                                                            ##STR61##                                                                               ##STR62##                                                                               O O H CH 176.5-180                              85                                                                                    ##STR63##                                                                            ##STR64##                                                                              OH        O O H CH 178.5-181                              86                                                                                    ##STR65##                                                                            ##STR66##                                                                               ##STR67##                                                                               O O H CH Unmeasurable                           __________________________________________________________________________

                                      TABLE 7                                      __________________________________________________________________________     Compound                               m.p. (°C.)                       No.   R.sup.1 R.sup.2                                                                              R         W X Yn                                                                               Z  or (n.sub.D.sup.20)                     __________________________________________________________________________     87                                                                                    ##STR68##                                                                             COOC.sub.2 H.sub.5                                                                    ##STR69##                                                                               O O H CH 85-90                                   88                                                                                    ##STR70##                                                                             COOC.sub.2 H.sub.5                                                                   OH        O O H CH 154-158                                 89                                                                                    ##STR71##                                                                             COOC.sub.2 H.sub.5                                                                    ##STR72##                                                                               O O H CH 1.5730                                  90                                                                                    ##STR73##                                                                             CN                                                                                    ##STR74##                                                                               O O H CH 152-156                                 91                                                                                    ##STR75##                                                                             CN    OH        O O H CH 165-169                                 92                                                                                    ##STR76##                                                                             CN    OCH.sub.3 O O H CH                                         93                                                                                    ##STR77##                                                                             CN                                                                                    ##STR78##                                                                               O O H CH 143-146                                 94                                                                                    ##STR79##                                                                              ##STR80##                                                                           OCH.sub.3 O O H CH 138-140                                 95                                                                                    ##STR81##                                                                              ##STR82##                                                                           OH        O O H CH                                         96                                                                                    ##STR83##                                                                             COCH.sub.3                                                                           OCH.sub.3 O O H CH 137-141                                 97                                                                                    ##STR84##                                                                             COCH.sub.3                                                                           OH        O O H CH                                         __________________________________________________________________________

                                      TABLE 8                                      __________________________________________________________________________     Compound                                 m.p. (°C.)                     No.   R.sup.1                                                                              R.sup.2                                                                              R         W X Yn    Z  or (n.sub.D.sup.20)                   __________________________________________________________________________      98   CH.sub.3                                                                             COOC.sub.2 H.sub.5                                                                   OH        O O 7-Cl  CH                                        99   CH.sub.3                                                                             COOC.sub.2 H.sub.5                                                                   OH        O O 7-CH.sub.3                                                                           CH                                       100   CH.sub.3                                                                             COOC.sub.2 H.sub.5                                                                   OH        O O 6-Cl  CH                                       101   CH.sub.3                                                                             COOC.sub.2 H.sub.5                                                                   OH        O O 6-CH.sub.3                                                                           CH                                       102   CH.sub.3                                                                             COOC.sub.2 H.sub.5                                                                   OH        O O 7-OCH.sub.3                                                                          CH                                       103   CH.sub.3                                                                             COOC.sub.2 H.sub.5                                                                   OH        O O 6-N(CH.sub.3).sub.2                                                                  CH                                       104   H     CH.sub.3                                                                             H         O S H     CH 158-161                               105   H     CH.sub.3                                                                             OH        O S H     CH 172-175                               106   H     CH.sub.3                                                                              ##STR85##                                                                               O S H     CH                                       107   H     CH.sub.3                                                                             OCH.sub.3 O S H     CH                                       108   COOCH.sub.3                                                                          CH.sub.3                                                                             H         O S H     CH 201-206                               109   COOCH.sub.3                                                                          CH.sub.3                                                                             OH        O S H     CH 154-158.5                             110   COOCH.sub.3                                                                          CH.sub.3                                                                              ##STR86##                                                                               O S H     CH                                       111   COOCH.sub.3                                                                          CH.sub.3                                                                              ##STR87##                                                                               O S H     CH                                       112   CH.sub.3                                                                             COOCH.sub.3                                                                          OH        O S H     CH 153-155                               113   CH.sub.3                                                                             COOCH.sub.3                                                                           ##STR88##                                                                               O S H     CH                                       114   CH.sub.3                                                                             COOCH.sub.3                                                                          OCH.sub.3 O S H     CH                                       115   CH.sub.3                                                                             COOCH.sub.3                                                                           ##STR89##                                                                               O S H     CH                                       116   CH.sub.3                                                                             COOC.sub.2 H.sub.5                                                                   OH        O S H     CH 155-158                               117   H     H     OH        O S H     CH                                       118   H     H                                                                                     ##STR90##                                                                               O S H     CH                                       __________________________________________________________________________

                                      TABLE 9                                      __________________________________________________________________________     Compound                                m.p. (°C.)                      No.   R.sup.1                                                                              R.sup.2                                                                              R          W X   Yn                                                                               Z  or (n.sub.D.sup.20)                    __________________________________________________________________________     119   H     H                                                                                     ##STR91## O S   H CH                                        120   H     H     OCH.sub.3  O S   H CH                                        121   H     H     OH         O S   H N                                         122   H     CH.sub.3                                                                             OH         O S   H N                                         123   H     CH.sub.3                                                                             OH         S S   H CH                                        124   H     CH.sub.3                                                                             OH         O NCH.sub.3                                                                          H CH                                        125   H     CH.sub.3                                                                             OH         O NCH.sub.3                                                                          H N                                         126   H     CH.sub.3                                                                             OH         S NCH.sub.3                                                                          H CH                                        127   COOCH.sub.3                                                                          CH.sub.3                                                                             OH         O NCH.sub.3                                                                          H CH                                        128   CH.sub.3                                                                             COOCH.sub.3                                                                           ##STR92## O O   H CH                                        129   CH.sub.3                                                                             COOCH.sub.3                                                                           ##STR93## O O   H N                                         130   CH.sub.3                                                                             COOCH.sub.3                                                                          O.sup.-  Na.sup.+                                                                         O O   H CH >300                                   131   CH.sub.3                                                                             COOC.sub.2 H.sub.5                                                                    ##STR94## O NH  H CH 196-199                                132   CH.sub.3                                                                             COOC.sub.2 H.sub.5                                                                   OH         O NH  H CH 202-204                                133   H     COCH.sub.3                                                                           OH         O O   H CH                                        __________________________________________________________________________

                                      TABLE 10                                     __________________________________________________________________________     Compound                                   m.p. (°C.)                   No.   R.sup.1                                                                             R.sup.2   R         W    X Yn                                                                               Z  or (n.sub.D.sup.20)                 __________________________________________________________________________     134   CH.sub.3                                                                            COOC.sub.2 H.sub.5                                                                       SCH.sub.3 O    O H CH                                     135   CH.sub.3                                                                            COOC.sub.2 H.sub.5                                                                       SC.sub.2 H.sub.5                                                                         O    O H CH                                     136   CH.sub.3                                                                            COOC.sub.2 H.sub.5                                                                        ##STR95##                                                                               O    O H CH                                     137   CH.sub.3                                                                            COOC.sub.2 H.sub.5                                                                       OH        N(CHO)                                                                              O H CH                                     138   CH.sub.3                                                                            COOC.sub.2 H.sub.5                                                                       OH        CH.sub.2                                                                            O H CH                                     139   CH.sub.3                                                                            COOC.sub.2 H.sub.5                                                                       OH        CH(CN)                                                                              O H CH                                     140   CH.sub.3                                                                            COOCH.sub.3                                                                              NH.sub.2  O    O H CH                                     141   CH.sub.3                                                                            COOCH.sub.3                                                                              NHCH.sub.3                                                                               O    O H CH                                     142   CH.sub.3                                                                            COOC.sub.2 H.sub.5                                                                       N(CH.sub.3).sub.2                                                                        O    O H CH                                     143   COCH.sub.3                                                                          CH.sub.3                                                                                  ##STR96##                                                                               O    O H CH                                     144   COCH.sub.3                                                                          CH.sub.3  OH        O    O H CH                                     145   COCH.sub.3                                                                          CH.sub.3                                                                                  ##STR97##                                                                               O    O H CH                                     146   CH.sub.3                                                                             ##STR98##                                                                                ##STR99##                                                                               O    O H CH                                     147   CH.sub.3                                                                             ##STR100##                                                                              OH        O    O H CH 143-146                             148   CH.sub.3                                                                             ##STR101##                                                                               ##STR102##                                                                              O    O H CH                                     149   CH.sub.3                                                                            COSCH.sub.3                                                                              OCH.sub.2 CHCH.sub.2                                                                     O    O H CH 134-136                             150   CH.sub.3                                                                            COSCH.sub.3                                                                              OH        O    O H CH 163-165                             151   CH.sub.3                                                                            COSCH.sub.3                                                                               ##STR103##                                                                              O    O H CH                                     152   CH.sub.3                                                                            COSC.sub.2 H.sub.5                                                                       OCH.sub.2 CHCH.sub.2                                                                     O    O H CH 102-105                             153   CH.sub.3                                                                            COSC.sub.2 H.sub.5                                                                       OH        O    O H CH 149-152                             __________________________________________________________________________

                                      TABLE 11                                     __________________________________________________________________________     Compound                           m.p. (°C.)                           No.   R.sup.1                                                                           R.sup.2                                                                               R         W X Yn                                                                               Z  or (n.sub.D.sup.20)                         __________________________________________________________________________     154   CH.sub.3                                                                          COSC.sub.2 H.sub.5                                                                     ##STR104##                                                                              O O H CH                                             155   CH.sub.3                                                                          CONHCH.sub.3                                                                          OCH.sub.2 CHCH.sub.2                                                                     O O H CH                                             156   CH.sub.3                                                                          CONHCH.sub.3                                                                          OH        O O H CH                                             157   CH.sub.3                                                                          CONHCH.sub.3                                                                           ##STR105##                                                                              O O H CH                                             158   CH.sub.3                                                                          CON(C.sub.2 H.sub.5).sub.2                                                            OCH.sub.2 CHCH.sub.2                                                                     O O H CH 96-98                                       159   CH.sub.3                                                                          CON(C.sub.2 H.sub.5).sub.2                                                            OH        O O H CH 183-186                                     160   CH.sub.3                                                                          CON(C.sub.2 H.sub.5).sub.2                                                             ##STR106##                                                                              O O H CH                                             161   CH.sub.3                                                                           ##STR107##                                                                           OCH.sub.2 CHCH.sub.2                                                                     O O H CH 85-88                                       162   CH.sub.3                                                                           ##STR108##                                                                           OH        O O H CH 180-182.5                                   163   CH.sub.3                                                                           ##STR109##                                                                            ##STR110##                                                                              O O H CH                                             164   CH.sub.3                                                                          COOC.sub.3 H.sub.7                                                                     ##STR111##                                                                              O O H CH 132-136                                     165   CH.sub.3                                                                          COOC.sub.3 H.sub.7                                                                     ##STR112##                                                                              O O H CH 108-109                                     166   CH.sub.3                                                                          COOC.sub.4 H.sub.9                                                                     ##STR113##                                                                              O O H CH 135-136.5                                   167   CH.sub.3                                                                          COOC.sub.4 H.sub.9                                                                     ##STR114##                                                                              O O H CH 1.5209                                      __________________________________________________________________________

                                      TABLE 12                                     __________________________________________________________________________     Compound                           m.p. (°C.)                           No.   R.sup.1                                                                           R.sup.2                                                                               R         W X Yn                                                                               Z  or (n.sub.D.sup.20)                         __________________________________________________________________________     168   CH.sub.3                                                                          COOC.sub.4 H.sub.9 -s                                                                  ##STR115##                                                                              O O H CH 149-150.5                                   169   CH.sub.3                                                                          COOC.sub.4 H.sub.9 -s                                                                  ##STR116##                                                                              O O H CH 90-91.5                                     170   CH.sub.3                                                                          COOC.sub.4 H.sub.9 -i                                                                  ##STR117##                                                                              O O H CH 152-156                                     171   CH.sub.3                                                                          COOC.sub.4 H.sub.9 -i                                                                 OH        O O H CH 135-138                                     172   CH.sub.3                                                                          COOC.sub.4 H.sub.9 -i                                                                  ##STR118##                                                                              O O H CH 1.5276                                      173   CH.sub.3                                                                          COOC.sub.4 H.sub.9 -t                                                                  ##STR119##                                                                              O O H CH 170-172                                     174   CH.sub.3                                                                          COOC.sub.4 H.sub.9 -t                                                                 OH        O O H CH 153-157                                     175   CH.sub.3                                                                          COOC.sub.4 H.sub.9 -t                                                                  ##STR120##                                                                              O O H CH                                             176   CH.sub.3                                                                          COOC.sub.4 H.sub.9 -t                                                                 OCH.sub.2 OC.sub.2 H.sub.5                                                               O O H CH                                             177   CH.sub.3                                                                          COOC.sub.5 H.sub.11                                                                    ##STR121##                                                                              O O H CH 115-116.5                                   178   CH.sub.3                                                                          COOC.sub.5 H.sub.11                                                                   OH        O O H CH 140-144                                     179   CH.sub.3                                                                          COOC.sub.5 H.sub.11                                                                    ##STR122##                                                                              O O H CH 1.5291                                      180   CH.sub.3                                                                          COOC.sub.5 H.sub.11                                                                   OCH.sub.2 OC.sub.2 H.sub.5                                                               O O H CH                                             181   CH.sub.3                                                                          COOC.sub.6 H.sub.13                                                                    ##STR123##                                                                              O O H CH 99-101                                      182   CH.sub.3                                                                          COOC.sub.6 H.sub.13                                                                   OH        O O H CH 153-159                                     __________________________________________________________________________

                                      TABLE 13                                     __________________________________________________________________________     Compound                            m.p. (°C.)                          No.   R.sup.1                                                                           R.sup.2 R         W X Yn                                                                               Z  or (n.sub.D.sup.20)                        __________________________________________________________________________     183   CH.sub.3                                                                          COOC.sub.6 H.sub.13                                                                     ##STR124##                                                                              O O H CH 1.5280                                     184   CH.sub.3                                                                          COOC.sub.6 H.sub.13                                                                    OCH.sub.2 OC.sub.2 H.sub.5                                                               O O H CH                                            185   CH.sub.3                                                                          COOC.sub.7 H.sub.15                                                                     ##STR125##                                                                              O O H CH 78-80                                      186   CH.sub.3                                                                          COOC.sub.7 H.sub.15                                                                    OH        O O H CH 145-149                                    187   CH.sub.3                                                                          COOC.sub.7 H.sub.15                                                                     ##STR126##                                                                              O O H CH 1.5288                                     188   CH.sub.3                                                                          COOC.sub.7 H.sub.15                                                                    OCH.sub.2 OC.sub.2 H.sub.5                                                               O O H CH                                            189   CH.sub.3                                                                          COOC.sub.8 H.sub.17                                                                     ##STR127##                                                                              O O H CH 105-108                                    190   CH.sub.3                                                                          COOC.sub.8 H.sub.17                                                                    OH        O O H CH 148-151                                    191   CH.sub.3                                                                          COOC.sub.8 H.sub.17                                                                     ##STR128##                                                                              O O H CH 1.5170                                     192   CH.sub.3                                                                           ##STR129##                                                                             ##STR130##                                                                              O O H CH 99-101                                     193   CH.sub.3                                                                           ##STR131##                                                                            OH        O O H CH 130-132                                    194   CH.sub.3                                                                           ##STR132##                                                                             ##STR133##                                                                              O O H CH 1.5260                                     195   CH.sub.3                                                                           ##STR134##                                                                            OCH.sub.2 OC.sub.2 H.sub.5                                                               O O H CH                                            196   CH.sub.3                                                                           ##STR135##                                                                             ##STR136##                                                                              O O H CH                                            197   CH.sub.3                                                                           ##STR137##                                                                            OH        O O H CH 115-119                                    __________________________________________________________________________

                                      TABLE 14                                     __________________________________________________________________________     Compound                              m.p. (°C.)                        No.   R.sup.1                                                                           R.sup.2 R           W X Yn                                                                               Z  or (n.sub.D.sup.20)                      __________________________________________________________________________     198   CH.sub.3                                                                           ##STR138##                                                                             ##STR139## O O H CH                                          199   CH.sub.3                                                                           ##STR140##                                                                            OCH.sub.2 OC.sub.2 H.sub.5                                                                 O O H CH                                          200   CH.sub.3                                                                          CONHC.sub.2 H.sub.5                                                                     ##STR141## O O H CH 147-149                                  201   CH.sub.3                                                                          CONHC.sub.2 H.sub.5                                                                    OH          O O H CH 200-203                                  202   CH.sub.3                                                                          CONHC.sub.2 H.sub.5                                                                    OCH.sub.2 CCH.sub.2                                                                        O O H CH Unmeasurable                             203   CH.sub.3                                                                          COOC.sub.3 H.sub.7 -i                                                                   ##STR142## O O H CH 140-143                                  204   CH.sub.3                                                                          COOC.sub.3 H.sub.7 -i                                                                  OH          O O H CH 167-170                                  205   CH.sub.3                                                                          COOC.sub.3 H.sub.7 -i                                                                   ##STR143## O O H CH Unmeasurable                             206   CH.sub.3                                                                          COOC.sub.3 H.sub.7 -i                                                                   ##STR144## O O H CH                                          207   CH.sub.3                                                                          COOC.sub.3 H.sub.7 -i                                                                  OCH.sub.2 OC.sub.2 H.sub.5                                                                 O O H CH                                          208   CH.sub.3                                                                          COOC.sub.3 H.sub.7 -i                                                                  O.sup.-  Na.sup.+                                                                          O O H CH 208-210                                  209   CH.sub.3                                                                          COOC.sub.3 H.sub.7 -i                                                                   ##STR145## O O H CH                                          210   CH.sub.3                                                                           ##STR146##                                                                             ##STR147## O O H CH 183-184.5                                211   CH.sub.3                                                                           ##STR148##                                                                            OH          O O H CH 161-164.5                                __________________________________________________________________________

                                      TABLE 15                                     __________________________________________________________________________     Compound                              m.p. (°C.)                        No.   R.sup.1                                                                           R.sup.2   R         W X Yn                                                                               Z  or (n.sub.D.sup.20)                      __________________________________________________________________________     212   CH.sub.3                                                                           ##STR149##                                                                               ##STR150##                                                                              O O H CH                                          213   CH.sub.3                                                                           ##STR151##                                                                               ##STR152##                                                                              O O H CH 194-196                                  214   CH.sub.3                                                                           ##STR153##                                                                              OH        O O H CH 103-105                                  215   CH.sub.3                                                                           ##STR154##                                                                               ##STR155##                                                                              O O H CH 1.5334                                   216   CH.sub.3                                                                           ##STR156##                                                                              OH        O O H CH 142-144                                  217   CH.sub.3                                                                           ##STR157##                                                                               ##STR158##                                                                              O O H CH                                          218   CH.sub.3                                                                          COOCH.sub.2 CHCH.sub.2                                                                    ##STR159##                                                                              O O H CH 101.5-104                                219   CH.sub.3                                                                          COOCH.sub.2 CHCH.sub.2                                                                   OH        O O H CH 163-165                                  220   CH.sub.3                                                                          COOCH.sub.2 CHCH.sub.2                                                                    ##STR160##                                                                              O O H CH                                          221   CH.sub.3                                                                          COOCH.sub.2 CHCH.sub.2                                                                    ##STR161##                                                                              O O H CH 1.5322                                   222   CH.sub.3                                                                          COOCH.sub.2 CCH                                                                           ##STR162##                                                                              O O H CH                                          223   CH.sub.3                                                                          COOCH.sub.2 CCH                                                                          OH        O O H CH 155-158                                  224   CH.sub.3                                                                          COOCH.sub.2 CCH                                                                          OCH.sub.2 CHCH.sub.2                                                                     O O H CH 93-95                                    __________________________________________________________________________

                                      TABLE 16                                     __________________________________________________________________________     Compound                             m.p. (°C.)                         No.   R.sup.1                                                                           R.sup.2  R         W X Yn                                                                               Z  or (n.sub.D.sup.20)                       __________________________________________________________________________     225   CH.sub.3                                                                          COOCH.sub.2 CCH                                                                          ##STR163##                                                                              O O H CH 70-73                                     226   CH.sub.3                                                                          COSC.sub.3 H.sub.7                                                                      OCH.sub.2 CHCH.sub.2                                                                     O O H CH 77-79                                     227   CH.sub.3                                                                          COSC.sub.3 H.sub.7                                                                      OH        O O H CH 130-133                                   228   CH.sub.3                                                                          COSC.sub.3 H.sub.7                                                                       ##STR164##                                                                              O O H CH                                           229   CH.sub.3                                                                          COSC.sub.3 H.sub.7                                                                      OCH.sub.2 OC.sub.2 H.sub.5                                                               O O H CH                                           230   CH.sub.3                                                                          COSC.sub.3 H.sub.7 -i                                                                   OCH.sub.2 CHCH.sub.2                                                                     O O H CH 105-108                                   231   CH.sub.3                                                                          COSC.sub.3 H.sub.7 -i                                                                   OH        O O H CH 160-163                                   232   CH.sub.3                                                                          COSC.sub.5 H.sub.11                                                                     OCH.sub.2 CHCH.sub.2                                                                     O O H CH 1.5621                                    233   CH.sub.3                                                                          COSC.sub.5 H.sub.11                                                                     OH        O O H CH 132-134                                   234   CH.sub.3                                                                          COSC.sub.4 H.sub.9                                                                      OCH.sub.2 CHCH.sub.2                                                                     O O H CH 1.5665                                    235   CH.sub.3                                                                          COSC.sub.4 H.sub.9                                                                      OH        O O H CH 127-130                                   236   CH.sub.3                                                                          COSC.sub.4 H.sub.9                                                                       ##STR165##                                                                              O O H CH 104-106                                   237   CH.sub.3                                                                          COSC.sub.4 H.sub.9 -i                                                                   OCH.sub.2 CHCH.sub.2                                                                     O O H CH 75-77                                     238   CH.sub.3                                                                          COSC.sub.4 H.sub.9 -i                                                                   OH        O O H CH                                           239   CH.sub.3                                                                          COSC.sub.4 H.sub.9 -i                                                                    ##STR166##                                                                              O O H CH                                           240   CH.sub.3                                                                          COSC.sub.4 H.sub.9 -t                                                                   OCH.sub.2 CHCH.sub.2                                                                     O O H CH                                           241   CH.sub.3                                                                          COSC.sub.4 H.sub.9 -t                                                                   OH        O O H CH 126-128                                   242   CH.sub.3                                                                          COSC.sub.4 H.sub.9 -t                                                                    ##STR167##                                                                              O O H CH                                           243   CH.sub.3                                                                           ##STR168##                                                                             OCH.sub.2 CHCH.sub.2                                                                     O O H CH                                           244   CH.sub.3                                                                           ##STR169##                                                                             OH        O O H CH                                           245   CH.sub.3                                                                           ##STR170##                                                                              ##STR171##                                                                              O O H CH                                           __________________________________________________________________________

                                      TABLE 17                                     __________________________________________________________________________     Compound                                   m.p. (°C.)                   No.   R.sup.1                                                                              R.sup.2     R         W X Yn                                                                               Z  or (n.sub.D.sup.20)                 __________________________________________________________________________     246   CH.sub.3                                                                             CON(CH.sub.3).sub.2                                                                         ##STR172##                                                                              O O H CH Unmeasurable                        247   CH.sub.3                                                                             CON(CH.sub.3).sub.2                                                                        OH        O O H CH 185-187                             248   CH.sub.3                                                                             CON(CH.sub.3).sub.2                                                                        OCH.sub.2 CHCH.sub.2                                                                     O O H CH Unmeasurable                        249   CH.sub.3                                                                              ##STR173##                                                                                 ##STR174##                                                                              O O H CH                                     250   CH.sub.3                                                                              ##STR175## OH        O O H CH 171-174                             251   CH.sub.3                                                                              ##STR176##                                                                                 ##STR177##                                                                              O O H CH                                     252   CH.sub.3                                                                             COOC.sub.2 H.sub.5                                                                          ##STR178##                                                                              O O H CH                                     253   CH.sub.3                                                                             COOC.sub.2 H.sub.5                                                                          ##STR179##                                                                              O O H CH                                     254   CH.sub.3                                                                             COCl        OCH.sub.2 CHCH.sub.2                                                                     O O H CH 75-78                               255   CH.sub.3                                                                             COCl                                                                                        ##STR180##                                                                              O O H CH 136-140                             256   Cl    COOC.sub.2 H.sub.5                                                                         OH        O O H CH                                     257   COOC.sub.2 H.sub.5                                                                   Cl          OH        O O H CH                                     258   CH.sub.3                                                                              ##STR181## OCH.sub.2 CHCH.sub.2                                                                     O O H CH 95-97                               259   CH.sub.3                                                                              ##STR182## OH        O O H CH 144.5-147                           260   CH.sub.3                                                                              ##STR183##                                                                                 ##STR184##                                                                              O O H CH                                     __________________________________________________________________________

                                      TABLE 18                                     __________________________________________________________________________     Compound                               m.p. (°C.)                       No.   R.sup.1                                                                            R.sup.2   R         W X Yn                                                                               Z  or (n.sub.D.sup.20)                     __________________________________________________________________________     261   CH.sub.3                                                                           COSCH.sub.2 CHCH.sub.2                                                                    ##STR185##                                                                              O O H CH                                         262   CH.sub.3                                                                           COSCH.sub.2 CHCH.sub.2                                                                   OH        O O H CH 1.5786                                  263   CH.sub.3                                                                           COSCH.sub.2 CHCH.sub.2                                                                    ##STR186##                                                                              O O H CH                                         264   CH.sub.3                                                                           COSCH.sub.2 CCH                                                                           ##STR187##                                                                              O O H CH                                         265   CH.sub.3                                                                           COSCH.sub.2 CCH                                                                          OH        O O H CH                                         266   CH.sub.3                                                                           COSCH.sub.2 CCH                                                                           ##STR188##                                                                              O O H CH                                         267   C.sub.3 H.sub.7                                                                    COOC.sub.2 H.sub.5                                                                        ##STR189##                                                                              O O H CH 102.5-105                               268   C.sub.3 H.sub.7                                                                    COOC.sub.2 H.sub.5                                                                       OH        O O H CH 140.5-144                               269   C.sub.3 H.sub.7                                                                    COOC.sub.2 H.sub.5                                                                        ##STR190##                                                                              O O H CH 1.5291                                  270   C.sub.2 H.sub.5                                                                    COOCH.sub.3                                                                               ##STR191##                                                                              O O H CH 115-117                                 271   C.sub.2 H.sub.5                                                                    COOCH.sub.3                                                                              OH        O O H CH 164-167                                 272   C.sub.2 H.sub.5                                                                    COOH                                                                                      ##STR192##                                                                              O O H CH 185-188                                 273   C.sub.3 H.sub.7 -i                                                                 COOC.sub.2 H.sub.5                                                                       OC.sub.2 H.sub.5                                                                         O O H CH 1.5459                                  274   C.sub.3 H.sub.7 -i                                                                 COOC.sub.2 H.sub.5                                                                       OH        O O H CH 157-159                                 275   C.sub.3 H.sub.7 -i                                                                 COOC.sub.2 H.sub.5                                                                        ##STR193##                                                                              O O H CH 1.5318                                  276   C.sub.2 H.sub.5                                                                    COOC.sub.2 H.sub.5                                                                       OC.sub.2 H.sub.5                                                                         O O H CH 1.5490                                  277   C.sub.3 H.sub.7                                                                    COOC.sub.2 H.sub.5                                                                       OC.sub.2 H.sub.5                                                                         O O H CH 1.5431                                  __________________________________________________________________________

                                      TABLE 19                                     __________________________________________________________________________     Compound                              m.p. (°C.)                        No.   R.sup.1                                                                           R.sup.2   R         W X Yn                                                                               Z  or (n.sub.D.sup.20)                      __________________________________________________________________________     278   CH.sub.3                                                                          COOC.sub.3 H.sub.6 Cl                                                                    OH        O O H CH 161-165                                  279   CH.sub.3                                                                          COOC.sub.3 H.sub.6 Cl                                                                     ##STR194##                                                                              O O H CH 124-125                                  280   CH.sub.3                                                                          COOC.sub.2 H.sub.4 F                                                                     OH        O O H CH 152-155                                  281   CH.sub.3                                                                          COOC.sub.2 H.sub.4 F                                                                      ##STR195##                                                                              O O H CH 114-117                                  282   CH.sub.3                                                                          COOC.sub.3 H.sub.6 Br                                                                     ##STR196##                                                                              O O H CH 124-127                                  283   CH.sub.3                                                                          COOC.sub.3 H.sub.6 Br                                                                    OH        O O H CH                                          284   CH.sub.3                                                                           ##STR197##                                                                              OCH.sub.2 CCH.sub.2                                                                      O O H CH 138-140                                  285   H  COOCH.sub.3                                                                               ##STR198##                                                                              O O H CH                                          286   H  COOCH.sub.3                                                                              OH        O O H CH 150-153                                  287   H  COOCH.sub.3                                                                               ##STR199##                                                                              O O H CH                                          288   H  COOC.sub.3 H.sub.7                                                                        ##STR200##                                                                              O O H CH                                          289   H  COOC.sub.3 H.sub.7                                                                       OH        O O H CH 158-161                                  290   H  COOC.sub.3 H.sub.7                                                                        ##STR201##                                                                              O O H CH                                          291   H  COOC.sub.3 H.sub.7 -i                                                                     ##STR202##                                                                              O O H CH 80-82                                    292   H  COOC.sub.3 H.sub.7 -i                                                                    OH        O O H CH 140-143.5                                293   H  COOC.sub.3 H.sub.7 -i                                                                     ##STR203##                                                                              O O H CH                                          __________________________________________________________________________

                                      TABLE 20                                     __________________________________________________________________________     Compound                          m.p. (°C.)                            No.   R.sup.1                                                                          R.sup.2                                                                               R         W X Yn                                                                               Z  or (n.sub.D.sup.20)                          __________________________________________________________________________     294   H COOC.sub.4 H.sub.9                                                                     ##STR204##                                                                              O O H CH 82-84                                        295   H COOC.sub.4 H.sub.9                                                                    OH        O O H CH 134-137                                      296   H COOC.sub.4 H.sub.9                                                                     ##STR205##                                                                              O O H CH                                              297   H COOC.sub.4 H.sub.9 -i                                                                  ##STR206##                                                                              O O H CH 95-98                                        298   H COOC.sub.4 H.sub.9 -i                                                                 OH        O O H CH 140-144                                      299   H COOC.sub.4 H.sub.9 -i                                                                  ##STR207##                                                                              O O H CH                                              300   H COOC.sub.4 H.sub.9 -s                                                                  ##STR208##                                                                              O O H CH 91-93                                        301   H COOC.sub.4 H.sub.9 -s                                                                 OH        O O H CH Unmeasurable                                 302   H COOC.sub.4 H.sub.9 -s                                                                  ##STR209##                                                                              O O H CH                                              303   H COOC.sub.4 H.sub.9 -t                                                                  ##STR210##                                                                              O O H CH                                              304   H COOC.sub.4 H.sub.9 -t                                                                 OH        O O H CH                                              305   H COOC.sub.4 H.sub.9 -t                                                                  ##STR211##                                                                              O O H CH                                              306   H COOC.sub.5 H.sub.11                                                                    ##STR212##                                                                              O O H CH 88-90                                        307   H COOC.sub.5 H.sub.11                                                                   OH        O O H CH 117-119                                      308   H COOC.sub.5 H.sub.11                                                                    ##STR213##                                                                              O O H CH                                              __________________________________________________________________________

                                      TABLE 21                                     __________________________________________________________________________     Compound                               m.p. (°C.)                       No.   R.sup.1                                                                           R.sup.2    R         W X Yn                                                                               Z  or (n.sub.D.sup.20)                     __________________________________________________________________________     309   H  COOC.sub.6 H.sub.13                                                                        ##STR214##                                                                              O O H CH                                         310   H  COOC.sub.6 H.sub.13                                                                       OH        O O H CH                                         311   H  COOC.sub.6 H.sub.13                                                                        ##STR215##                                                                              O O H CH                                         312   H                                                                                  ##STR216##                                                                                ##STR217##                                                                              O O H CH                                         313   H                                                                                  ##STR218##                                                                               OH        O O H CH                                         314   H                                                                                  ##STR219##                                                                                ##STR220##                                                                              O O H CH                                         315   CH.sub.3                                                                          CONHC.sub.3 H.sub.7 -i                                                                     ##STR221##                                                                              O O H CH Unmeasurable                            316   CH.sub.3                                                                          CONHC.sub.3 H.sub.7 -i                                                                    OH        O O H CH 173-176                                 317   CH.sub.3                                                                          CONHC.sub.3 H.sub.7 -i                                                                    OCH.sub.2 CHCH.sub.2                                                                     O O H CH   157-159.5                             318   CH.sub.3                                                                           ##STR222##                                                                               OCH.sub.2 CHCH.sub.2                                                                     O O H CH 137-139                                 319   CH.sub.3                                                                           ##STR223##                                                                               OH        O O H CH 137-138                                 320   CH.sub.3                                                                           ##STR224##                                                                                ##STR225##                                                                              O O H CH                                         321   CH.sub.3                                                                          COOCH.sub.2 C.sub.4 H.sub.9 -t                                                             ##STR226##                                                                              O O H CH 162-165                                 322   CH.sub.3                                                                          COOCH.sub.2 C.sub.4 H.sub.9 -t                                                            OH        O O H CH 137-140                                 323   CH.sub.3                                                                          COOCH.sub.2 C.sub.4 H.sub.9 -t                                                             ##STR227##                                                                              O O H CH                                         __________________________________________________________________________

                                      TABLE 22                                     __________________________________________________________________________     Compound                               m.p. (°C.)                       No.   R.sup.1                                                                           R.sup.2  R           W X Yn                                                                               Z  or (n.sub.D.sup.20)                     __________________________________________________________________________     324   CH.sub.3                                                                          COOCH.sub.2 C.sub.4 H.sub.9 -t                                                          OCH.sub.2 OC.sub.2 H.sub.5                                                                 O O H CH                                         325   CH.sub.3                                                                           ##STR228##                                                                              ##STR229## O O H CH 149-151                                 326   CH.sub.3                                                                           ##STR230##                                                                             OH          O O H CH 146-148                                 327   CH.sub.3                                                                           ##STR231##                                                                              ##STR232## O O H CH 1.5330                                  328   CH.sub.3                                                                           ##STR233##                                                                             OCH.sub.2 OC.sub.2 H.sub.5                                                                 O O H CH                                         329   CH.sub.3                                                                           ##STR234##                                                                             OH          O O H CH 173-175                                 330   CH.sub.3                                                                          COOC.sub.3 H.sub.7                                                                      O.sup.-  Na.sup.+                                                                          O O H CH                                         331   CH.sub.3                                                                          COOC.sub.3 H.sub.7                                                                       ##STR235## O O H CH                                         332   CH.sub.3                                                                          COOC.sub.3 H.sub.7                                                                      OCH.sub.2 CHCH.sub.2                                                                       O O H CH                                         333   CH.sub.3                                                                          COOC.sub.3 H.sub.7                                                                       ##STR236## O O H CH                                         334   CH.sub.3                                                                          COOC.sub.3 H.sub.7                                                                      N(CH.sub.3).sub.2                                                                          O O H CH                                         335   CH.sub.3                                                                          COOC.sub.3 H.sub.7                                                                       ##STR237## O O H CH                                         336   CH.sub.3                                                                           ##STR238##                                                                              ##STR239## O O H CH Unmeasurable                            337   CH.sub.3                                                                           ##STR240##                                                                             OH          O O H CH 138-143                                 __________________________________________________________________________

                                      TABLE 23                                     __________________________________________________________________________     Compound                                m.p. (°C.)                      No.   R.sup.1                                                                            R.sup.2   R          W X Yn                                                                               Z  or (n.sub.D.sup.20)                    __________________________________________________________________________     338   CH.sub.3                                                                            ##STR241##                                                                              OH         O O H CH                                        339   CH.sub.3                                                                           COOCH.sub.2 OC.sub.2 H.sub.5                                                              ##STR242##                                                                               O O H CH 110-113                                340   CH.sub.3                                                                           COOCH.sub.2 OC.sub.2 H.sub.5                                                             OH         O O H CH 152-154                                341   CH.sub.3                                                                           COOC.sub.2 H.sub.4 SCH.sub.3                                                             OH         O O H CH 140-143                                342   CH.sub.3                                                                           COOC.sub.2 H.sub.4 SCH.sub.3                                                             OCH.sub.2 CHCH.sub.2                                                                      O O H CH 64-66                                  343   CH.sub.3                                                                           COOCH(CF.sub.3).sub.2                                                                     ##STR243##                                                                               O O H CH   158-160.5                            344   CH.sub.3                                                                           COOCH(CF.sub.3).sub.2                                                                    OH         O O H CH 137-140                                345   CH.sub.3                                                                           COOCH.sub.3                                                                              O.sup.-  H.sub.3.sup.+ NCH(CH.sub.3).sub.2                                                O O H CH 133.5-137                              346   CH.sub.3                                                                            ##STR244##                                                                              OH         O O H CH 189-191                                347   CH.sub.3                                                                           COOC.sub.2 H.sub.4 OCH.sub.3                                                              ##STR245##                                                                               O O H CH 105-107                                348   CH.sub.3                                                                           COOC.sub.2 H.sub.4 OCH.sub.3                                                             OH         O O H CH 138-142                                349   CH.sub.3                                                                           COOC.sub.2 H.sub.4 OCH.sub.3                                                              ##STR246##                                                                               O O H CH                                        350                                                                                   ##STR247##                                                                        COOCH.sub.3                                                                               ##STR248##                                                                               O O H CH                                        351                                                                                   ##STR249##                                                                        COOCH.sub.3                                                                              OH         O O H CH                                        352                                                                                   ##STR250##                                                                        COOCH.sub.3                                                                               ##STR251##                                                                               O O H CH                                        __________________________________________________________________________

                                      TABLE 24                                     __________________________________________________________________________     Compound                                     m.p. (°C.)                 No.   R.sup.1                                                                            R.sup.2         R         W X Yn                                                                               Z  or (n.sub.D.sup.20)               __________________________________________________________________________     353                                                                                   ##STR252##                                                                        COOCH.sub.3     OCH.sub.2 OC.sub.2 H.sub.5                                                               O O H CH                                   354   CH.sub.3                                                                           COOCH.sub.2 SCH.sub.3                                                                          OCH.sub.2 CHCH.sub.2                                                                     O O H CH  99-101                           355   CH.sub.3                                                                           COOCH.sub.2 SCH.sub.3                                                                          OH        O O H CH   152-155.5                       356   CH.sub.3                                                                           COOCH.sub.2 CF.sub.3                                                                           OH        O O H CH 152.5-155                         357   CH.sub.3                                                                           COOCH.sub.2 CF.sub.3                                                                           OCH.sub.2 CHCH.sub.2                                                                     O O H CH 114-116                           358   CH.sub.3                                                                           COOCH.sub.2 CF.sub.3                                                                            ##STR253##                                                                              O O H CH                                   359   CH.sub.3                                                                           COOH                                                                                            ##STR254##                                                                              O O H CH 222-225                           360   CH.sub.3                                                                           COC.sub.2 H.sub.5                                                                               ##STR255##                                                                              O O H CH                                   361   CH.sub.3                                                                           COC.sub.2 H.sub.5                                                                              OH        O O H CH                                   362   CH.sub.3                                                                           COC.sub.3 H.sub.7                                                                               ##STR256##                                                                              O O H CH                                   363   CH.sub.3                                                                           COC.sub.3 H.sub.7                                                                              OH        O O H CH                                   364   CH.sub.3                                                                           COC.sub.4 H.sub.9                                                                               ##STR257##                                                                              O O H CH 119-121                           365   CH.sub.3                                                                           COC.sub.4 H.sub.9                                                                              OH        O O H CH 136-138                           366   CH.sub.3                                                                           COC.sub.5 H.sub.11                                                                              ##STR258##                                                                              O O H CH 106-109                           367   CH.sub.3                                                                           COC.sub.5 H.sub.11                                                                             OH        O O H CH 130-132                           368   CH.sub.3                                                                            ##STR259##     OH        O O H CH Unmeasurable                      369   CH.sub.3                                                                            ##STR260##                                                                                     ##STR261##                                                                              O O H CH 1.5519                            __________________________________________________________________________

                                      TABLE 25                                     __________________________________________________________________________     Compound                                m.p. (°C.)                      No.   R.sup.1                                                                              R.sup.2  R         W X Yn                                                                               Z  or (n.sub.D.sup.20)                    __________________________________________________________________________     370   CH.sub.3                                                                             COOH                                                                                     ##STR262##                                                                              O O H CH 132-135                                371   CH.sub.3                                                                             COOH     OCH.sub.2 CHCH.sub.2                                                                     O O H CH 207-210                                372   H     COOCH.sub.2 C.sub.4 H.sub.9 -t                                                          OH        O O H CH                                        373   H     COSC.sub.2 H.sub.5                                                                      OH        O O H CH                                        374   H     CONHC.sub.2 H.sub.5                                                                     OH        O O H CH                                        375   H     CON(CH.sub.3).sub.2                                                                     OH        O O H CH                                        376   H     COSC.sub.3 H.sub.7                                                                      OH        O O H CH                                        377   H     COSC.sub.4 H.sub.9                                                                      OH        O O H CH                                        378   CH.sub.3 OCH.sub.2                                                                   COOCH.sub.3                                                                              ##STR263##                                                                              O O H CH 92-95                                  379   CH.sub.3 OCH.sub.2                                                                   COOCH.sub.3                                                                             OH        O O H CH 150-153                                380   CH.sub.3 OCH.sub.2                                                                   COOC.sub.2 H.sub.5                                                                       ##STR264##                                                                              O O H CH                                        381   CH.sub.3 OC.sub.2 H.sub.4                                                            COOCH.sub.3                                                                              ##STR265##                                                                              O O H CH                                        382   CH.sub.3 OC.sub.2 H.sub.4                                                            COOCH.sub.3                                                                             OH        O O H CH                                        383   CH.sub.3 OC.sub.2 H.sub.4                                                            COOCH.sub.3                                                                              ##STR266##                                                                              O O H CH                                        __________________________________________________________________________

                                      TABLE 26                                     __________________________________________________________________________      ##STR267##                                                                    Compound                             m.p. (°C.)                         No.   R.sup.2                                                                              R.sup.3                                                                             R.sup.4                                                                             R         W Z  or (n.sub.D.sup.20)                       __________________________________________________________________________     384   COOCH.sub.3                                                                          CH.sub.3                                                                            CH.sub.3                                                                             ##STR268##                                                                              O CH 145-147                                   385   COOCH.sub.3                                                                          CH.sub.3                                                                            CH.sub.3                                                                            OH        O CH 174-177                                   386   COOCH.sub.3                                                                          CH.sub.3                                                                            OCH.sub.3                                                                           OH        O CH 138-140                                   387   COOCH.sub.3                                                                          CH.sub.3                                                                            Cl   OH        O CH                                           388   COOCH.sub.3                                                                          CH.sub.3                                                                            OCH.sub.3                                                                            ##STR269##                                                                              O CH 102.5-106                                 389   COOCH.sub.3                                                                          CH.sub.3                                                                            OCH.sub.3                                                                           OH        O N  143-146                                   390   COOCH.sub.3                                                                          CH.sub.3                                                                            OCH.sub.3                                                                            ##STR270##                                                                              O N  117-120                                   391   COOCH.sub.3                                                                          OCH.sub.3                                                                           Cl   OH        O CH 162-164                                   392   COOCH.sub.3                                                                          OCH.sub.3                                                                           NHCH.sub.3                                                                          OH        O CH                                           393   COOCH.sub.3                                                                          OCH.sub.3                                                                           OCHF.sub.2                                                                          OH        O CH 151-155                                   394   COOCH.sub.3                                                                          OCHF.sub.2                                                                          OCHF.sub.2                                                                          OH        O CH                                           395   COOCH.sub.3                                                                          OCH.sub.3                                                                           N(CH.sub.3).sub.2                                                                   OH        O CH 167-170                                   396   COOCH.sub.3                                                                          CH.sub.3                                                                            CH.sub.3                                                                             ##STR271##                                                                              O N                                            397   COOCH.sub.3                                                                          CH.sub.3                                                                            OCH.sub.3                                                                            ##STR272##                                                                              O CH                                           398   COOCH.sub.3                                                                          Cl   OCH.sub.3                                                                            ##STR273##                                                                              O CH 129-132                                   __________________________________________________________________________

                                      TABLE 27                                     __________________________________________________________________________      ##STR274##                                                                    Compound                             m.p. (°C.)                         No.   R.sup.1                                                                              R.sup.2                                                                              R         W X   Z  or (n.sub.D.sup.20)                       __________________________________________________________________________     399   H     H     H         O S   CH                                           400   H     H     OH        O S   CH                                           401   H     H                                                                                     ##STR275##                                                                              O S   CH                                           402   H     H     H         O NCH.sub.3                                                                          CH                                           403   H     H     OH        O NCH.sub.3                                                                          CH                                           404   H     H                                                                                     ##STR276##                                                                              O NCH.sub.3                                                                          CH                                           405   H     COOC.sub.2 H.sub.5                                                                   H         O O   CH 116-124                                   406   H     COOC.sub.2 H.sub.5                                                                   OH        O O   CH                                           407   H     COOC.sub.2 H.sub.5                                                                    ##STR277##                                                                              O O   CH                                           408   CH.sub.3                                                                             COOC.sub.2 H.sub.5                                                                   H         O O   CH                                           409   CH.sub.3                                                                             COOC.sub.2 H.sub.5                                                                   OH        O O   CH                                           410   H     COOC.sub.2 H.sub.5                                                                   OH        O NCH.sub.3                                                                          CH                                           411   H     COOC.sub.2 H.sub.5                                                                   OH        O S   CH                                           412   COOC.sub.2 H.sub.5                                                                   H     H         O O   CH                                           413   COOC.sub.2 H.sub.5                                                                   H     OH        O O   CH                                           414   COOC.sub.2 H.sub.5                                                                   H     H         O NCH.sub.3                                                                          CH                                           415   COOC.sub.2 H.sub.5                                                                   H     H         O NCH.sub.3                                                                          N                                            416   COOC.sub.2 H.sub.5                                                                   CH.sub.3                                                                             OH        O O   CH                                           417   COOC.sub.2 H.sub.5                                                                   H     OH        O NCH.sub.3                                                                          CH                                           418   COOC.sub.2 H.sub.5                                                                   H     H         O S   CH                                           419   COOC.sub.2 H.sub.5                                                                   H     OH        O S   CH                                           420   COOC.sub.2 H.sub.5                                                                   H     H         S S   CH                                           421   COOC.sub.2 H.sub.5                                                                   H     OH        O S   CH                                           422   H     CH.sub.3                                                                              ##STR278##                                                                              O NCH.sub.3                                                                          CH                                           __________________________________________________________________________

                                      TABLE 28                                     __________________________________________________________________________     Compound                            m.p. (°C.)                          No.   R.sup.1                                                                          R.sup.2                                                                           R        W X          Z  or (n.sub.D.sup.20)                        __________________________________________________________________________     423   H CH.sub.3                                                                          OH       O NCH.sub.3  CH                                            424   H H  OCH.sub.2 OCH.sub.3                                                                     O NCH.sub.2 CHCH.sub.2                                                                      CH                                            425   H H  OH       O NCH.sub.2 CHCH.sub.2                                                                      CH                                            426   H CH.sub.3                                                                          OCH.sub.2 OCH.sub.3                                                                     O NCH.sub.2 CHCH.sub.2                                                                      CH                                            427   H CH.sub.3                                                                          OH       O NCH.sub.2 CHCH.sub.2                                                                      CH                                            428   H CH.sub.3                                                                          OCH.sub.2 CHCH.sub.2                                                                    O NCH.sub.2 COOCH.sub.3                                                                     CH                                            429   H CH.sub.3                                                                          OH       O NCH.sub.2 COOCH.sub.3                                                                     CH                                            430   H CH.sub.3                                                                           ##STR279##                                                                             O NC(O)CH.sub.3                                                                             CH                                            431   H CH.sub.3                                                                          OH       O NC(O)CH.sub.3                                                                             CH                                            432   H CH.sub.3                                                                           ##STR280##                                                                             O                                                                                 ##STR281##                                                                               CH                                            433   H CH.sub.3                                                                          OH       O                                                                                 ##STR282##                                                                               CH                                            434   H CH.sub.3                                                                           ##STR283##                                                                             O NCOOC.sub.2 H.sub.5                                                                       CH                                            435   H CH.sub.3                                                                          OH       O NCOOC.sub.2 H.sub.5                                                                       CH                                            436   H CH.sub.3                                                                           ##STR284##                                                                             O                                                                                 ##STR285##                                                                               CH                                            437   H CH.sub.3                                                                          OH       O                                                                                 ##STR286##                                                                               CH                                            438   H CH.sub.3                                                                           ##STR287##                                                                             O                                                                                 ##STR288##                                                                               CH                                            439   H CH.sub.3                                                                          OH       O                                                                                 ##STR289##                                                                               CH                                            440   H CH.sub.3                                                                          OCH.sub.2 CHCH.sub.2                                                                    O NSO.sub.2 CH.sub.3                                                                        CH                                            441   H CH.sub.3                                                                          OH       O NSO.sub.2 CH.sub.3                                                                        CH                                            442   H CH.sub.3                                                                           ##STR290##                                                                             O NH         CH                                            443   H CH.sub.3                                                                          OH       O NH         CH                                            444   H CH.sub.3                                                                          OH       O NH         N                                             __________________________________________________________________________

                                      TABLE 29                                     __________________________________________________________________________      ##STR291##                                                                    Compound                          m.p. (°C.)                            No.   R.sup.1                                                                              R             W X  Z  or (n.sub.D.sup.20)                          __________________________________________________________________________     445   H                                                                                     ##STR292##   O O  CH Unmeasurable                                 446   H     OCH.sub.3     O O  CH 144-148                                      447   H     OH            O O  CH                                              448   H     OH            O O  N                                               449   H     OH            S O  CH                                              450   H     OH            S O  N                                               451   CH.sub.3                                                                             OH            O O  CH                                              452   C.sub.2 H.sub.5                                                                      OH            O O  CH                                              453                                                                                   ##STR293##                                                                          OH            O O  CH                                              454   H     OH            O NH CH                                              455   CH.sub.3                                                                             OH            O NH CH                                              456   H     OH            O NH N                                               457   H     OH            O S  CH                                              458   CH.sub.3                                                                             OH            O S  CH                                              459   H     OH            O S  N                                               460   CH.sub.3                                                                             OH            O S  N                                               __________________________________________________________________________

                                      TABLE 30                                     __________________________________________________________________________      ##STR294##                                                                    Compound                            m.p. (°C.)                          No.   R.sup.1                                                                              R.sup.3                                                                            R.sup.4                                                                            R       W  X Z  or (n.sub.D.sup.20)                        __________________________________________________________________________     461   H     OCH.sub.3                                                                          OCH.sub.3                                                                          OC.sub.2 H.sub.5                                                                       O  O CH 111-114                                    462   H     OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                                                              O  O CH 125-127                                    463   H     OCH.sub.3                                                                          OCH.sub.3                                                                          OH      O  O CH 168-174                                    464   H     OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                                                              O  O N  141-144                                    465   H     OCH.sub.3                                                                          OCH.sub.3                                                                          OH      O  O N                                             466   H     OCH.sub.3                                                                          OCH.sub.3                                                                          OH      S  O CH                                            467   H     OCH.sub.3                                                                          OCH.sub.3                                                                          OH      S  O N                                             468   CH.sub.3                                                                             OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                                                              O  O CH 162-165                                    469   CH.sub.3                                                                             OCH.sub.3                                                                          OCH.sub.3                                                                          OH      O  O CH 204-210                                    470   CH.sub.3                                                                             OCH.sub.3                                                                          OCH.sub.3                                                                          OH      O  O N                                             471   CH.sub.3                                                                             OCH.sub.3                                                                          OCH.sub.3                                                                          OH      S  O CH                                            472   H     OCH.sub.3                                                                          OCH.sub.3                                                                          OC.sub.2 H.sub.4 Si(CH.sub.3).sub.3                                                    O  O CH 1.5343                                     473   CH.sub.3                                                                             OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.2 OC.sub.2 H.sub.5                                                             O  O N                                             474   C.sub.2 H.sub.5                                                                      OCH.sub.3                                                                          OCH.sub.3                                                                          OH      O  O CH                                            475                                                                                   ##STR295##                                                                          OCH.sub.3                                                                          OCH.sub.3                                                                          OH      O  O CH 210-211                                    476   H     CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                              O  O CH 1.5582                                     477   H     OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.2 OC.sub.2 H.sub.5                                                             O  O CH Unmeasurable                               478   H     OCH.sub.3                                                                          OCH.sub.3                                                                          OH      O  S CH                                            479   CH.sub.3                                                                             OCH.sub.3                                                                          OCH.sub.3                                                                          OH      O  S CH                                            480   H     OCH.sub.3                                                                          OCH.sub.3                                                                          OH      O  S N                                             481   CH.sub.3                                                                             OCH.sub.3                                                                          OCH.sub.3                                                                          OH      O  S N                                             482   CH.sub.2 NO.sub.2                                                                    OCH.sub.3                                                                          OCH.sub.3                                                                          OH      O  S CH 168-169                                    483   CH.sub.3                                                                             OCH.sub.3                                                                          OCH.sub.3                                                                          OH                                                                                      ##STR296##                                                                       O CH                                            __________________________________________________________________________

                  TABLE 31                                                         ______________________________________                                          ##STR297##                                                                    Compound                                 m.p. (°C.)                     No.     R.sup.1 R       W    X     Z     or (n.sub.D.sup.20)                   ______________________________________                                         484     H       OH      O    O     CH                                          485     H       OH      S    O     CH                                          486     H       OH      O    O     N                                           487     CH.sub.3                                                                               OCH.sub.3                                                                              O    O     CH    167-171                               488     CH.sub.3                                                                               OH      O    O     CH    155-159                               489     CH.sub.3                                                                               OH      O    O     N                                           490     CH.sub.3                                                                               OH      S    O     N                                           491     CH.sub.3                                                                               OH      S    O     CH                                          492     H       OH      O    S     CH                                          493     H       OH      O    S     N                                           494     H       OH      O    NH    CH                                          495     H       OH      O    NCH.sub.3                                                                            CH                                          ______________________________________                                    

                                      TABLE 32                                     __________________________________________________________________________      ##STR298##                                                                    Compound                         m.p. (°C.)                             No.   R.sup.1                                                                            R.sup.3                                                                            R.sup.4                                                                            R  W  X     Z  or (n.sub.D.sup.20)                           __________________________________________________________________________     496   H   OCH.sub.3                                                                          OCH.sub.3                                                                          OH O  O     CH                                               497   H   OCH.sub.3                                                                          OCH.sub.3                                                                          OH S  O     CH                                               498   H   OCH.sub.3                                                                          OCH.sub.3                                                                          OH O  NH    CH 169-171                                       499   CH.sub.3                                                                           OCH.sub.3                                                                          OCH.sub.3                                                                          OH O  O     CH                                               500   CH.sub.3                                                                           OCH.sub.3                                                                          OCH.sub.3                                                                          OH O  O     N                                                501   CH.sub.3                                                                           OCH.sub.3                                                                          OCH.sub.3                                                                          OH S  O     N                                                502   CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           OH O  O     CH                                               503   CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                          OH O  O     CH                                               504   H   OCH.sub.3                                                                          OCH.sub.3                                                                          OH O  S     CH                                               505   H   OCH.sub.3                                                                          OCH.sub.3                                                                          OH O  S     N                                                506   H   OCH.sub.3                                                                          OCH.sub.3                                                                          OH O  NCOCH.sub.3                                                                          CH 175-178                                       __________________________________________________________________________

                                      TABLE 33                                     __________________________________________________________________________      ##STR299##                                                                    Compound                       m.p. (°C.)                               No.   R.sup.1                                                                            R.sup.2                                                                             R         W  Z  or (n.sub.D.sup.20)                             __________________________________________________________________________     507   OC.sub.2 H.sub.5                                                                   H    OCH.sub.3 O  CH 1.5243                                          508   OC.sub.2 H.sub.5                                                                   H    OH        O  CH 1.5306                                          509   CH.sub.3                                                                           H    OCH.sub.3 O  CH 1.5319                                          510   CH.sub.3                                                                           H    OH        O  CH Unmeasurable                                    511   CH.sub.3                                                                           H    OCH.sub.3 O  N                                                  512   CH.sub.3                                                                           H    OH        O  N                                                  513   CH.sub.3                                                                           H    OCH.sub.3 S  CH                                                 514   CH.sub.3                                                                           H    OH        S  CH                                                 515   OC.sub.2 H.sub.5                                                                   H    OCH.sub.3 O  N                                                  516   OC.sub.2 H.sub.5                                                                   H    OH        O  N                                                  517   OC.sub.2 H.sub.5                                                                   H    OH        S  CH                                                 518   OC.sub.2 H.sub.5                                                                   H    OH        S  N                                                  519   OC.sub.2 H.sub.5                                                                   CH.sub.3                                                                             ##STR300##                                                                              O  CH 1.5575                                          520   OC.sub.2 H.sub.5                                                                   CH.sub.3                                                                            OH        O  CH 105-109                                         521   OC.sub.2 H.sub.5                                                                   CH.sub.3                                                                             ##STR301##                                                                              O  CH                                                 522   OC.sub.2 H.sub.5                                                                   CN                                                                                   ##STR302##                                                                              O  CH                                                 523   OC.sub.2 H.sub.5                                                                   CN   OH        O  CH                                                 524   OC.sub.2 H.sub.5                                                                   CN                                                                                   ##STR303##                                                                              O  CH                                                 525   OC.sub.2 H.sub.5                                                                   COCH.sub.3                                                                           ##STR304##                                                                              O  CH                                                 526   OC.sub.2 H.sub.5                                                                   COCH.sub.3                                                                          OH        O  CH                                                 527   OC.sub.2 H.sub.5                                                                   COCH.sub.3                                                                           ##STR305##                                                                              O  CH                                                 __________________________________________________________________________

                                      TABLE 34                                     __________________________________________________________________________      ##STR306##                                                                    Compound                            m.p. (°C.)                          No.   R.sup.1                                                                           R.sup.2      R           X or (n.sub.D.sup.20)                        __________________________________________________________________________     528   CH.sub.3                                                                          COOC.sub.2 H.sub.4 SCH.sub.3                                                                OCH.sub.2 OCOC.sub.4 H.sub.9 -t                                                            O 69-71                                      529   CH.sub.3                                                                          COOH         OCH.sub.2 OC.sub.2 H.sub.4 OCH.sub.3                                                       O 139-141                                    530   CH.sub.3                                                                          COOCH.sub.2 CHCHCH.sub.3                                                                    OCH.sub.2 OC.sub.2 H.sub.4 OCH.sub.3                                                       O 1.5441                                     531   CH.sub.3                                                                          COOCH.sub.2 CHCHCl                                                                          OCH.sub.2 OC.sub.2 H.sub.4 OCH.sub.3                                                       O Unmeasurable                               532   CH.sub.3                                                                          COOCH.sub.2 CClCHCl                                                                         OCH.sub.2 OC.sub.2 H.sub.4 OCH.sub.3                                                       O 1.5488                                     533   CH.sub.3                                                                          COOCH.sub.2 CHCHCH.sub.3                                                                    OH          O 143-144                                    534   CH.sub.3                                                                          COOCH.sub.2 CHCHCl                                                                          OH          O 146-148                                    535   CH.sub.3                                                                          COOCH.sub.2 CClCHCl                                                                         OH          O 155-158                                    536   CH.sub.3                                                                           ##STR307##  OCH.sub.2 CHCH.sub.2                                                                       O 191-194                                    537   CH.sub.3                                                                           ##STR308##  OCH.sub.2 CHCH.sub.2                                                                       O 128-131                                    538   CH.sub.3                                                                          CONHC.sub.3 H.sub.7 -i                                                                      OCH.sub.2 OCOC.sub.4 H.sub.9 -t                                                            O   183-184.5                                539   CH.sub.3                                                                          COSC.sub.5 H.sub.11                                                                         OCH(CH.sub.3)OCOC.sub.4 H.sub.9 -t                                                         O 1.5380                                     540   CH.sub.3                                                                          COONC(CH.sub.3).sub.2                                                                       OCH(CH.sub.3)OCOC.sub.4 H.sub.9 -t                                                         O 186-189                                    541   H  COOCH.sub.2 CHCH.sub.2                                                                       ##STR309## O 85-87                                      542   H  COOH                                                                                         ##STR310## O 174-175                                    543   CH.sub.3                                                                           ##STR311##  OCH.sub.2 CHCH.sub.2                                                                       O 114-116                                    544   CH.sub.3                                                                          CONHC.sub.4 H.sub.9                                                                         OCH.sub.2 CHCH.sub.2                                                                       O 148-150                                    545   CH.sub.3                                                                          COOCH.sub.2 C(CH.sub.3)CH.sub.2                                                             OCH.sub.2 OC.sub.2 H.sub.4 OCH.sub.3                                                       O 1.5438                                     546   CH.sub.3                                                                          COOCH(CH.sub.3)CHCH.sub.2                                                                   OCH.sub.2 OC.sub.2 H.sub.4 OCH.sub.3                                                       O 1.5373                                     547   CH.sub.3                                                                          COOCH.sub.2 CHC(CH.sub.3).sub.2                                                             OCH.sub.2 OC.sub.2 H.sub.4 OCH.sub.3                                                       O 1.5461                                     548   CH.sub.3                                                                          COOCH.sub.2 CCCH.sub.3                                                                      OCH.sub.2 OC.sub.2 H.sub.4 OCH.sub.3                                                       O 69-71                                      549   CH.sub.3                                                                          COOCH.sub.2 CH.sub.2 CCH                                                                    OCH.sub.2 OC.sub.2 H.sub.4 OCH.sub.3                                                       O 66-68                                      550   CH.sub.3                                                                          COOCH(CH.sub.3)CCH                                                                          OCH.sub.2 OC.sub.2 H.sub.4 OCH.sub.3                                                       O 1.5420                                     551   CH.sub.3                                                                          COOCH(CH.sub.3)CHCH.sub.2                                                                   OH          O   140-144.5                                __________________________________________________________________________

                                      TABLE 35                                     __________________________________________________________________________     Compound                            m.p. (°C.)                          No.   R.sup.1                                                                           R.sup.2      R           X or (n.sub.D.sup.20)                        __________________________________________________________________________     552   CH.sub.3                                                                          COOCH.sub.2 CCCH.sub.3                                                                      OH          O 174-178                                    553   CH.sub.3                                                                          COOCH.sub.2 CH.sub.2 CCH                                                                    OH          O Unmeasurable                               554   CH.sub.3                                                                          COOCH(CH.sub.3)CCH                                                                          OH          O 160-165                                    555   CH.sub.3                                                                          COSCH(CH.sub.3)C.sub.2 H.sub.5                                                              OCH.sub.2 CHCH.sub.2                                                                       O 100-103                                    556   CH.sub.3                                                                          COOC.sub.3 H.sub.7                                                                          OCH(CH.sub.3)OCOC.sub.4 H.sub.9                                                            O 102-106                                    557   CH.sub.3                                                                          COOC.sub.3 H.sub.7                                                                          OCH(CH.sub.3)OCOC.sub.4 H.sub.9 -t                                                         O 126-129                                    558   CH.sub.3                                                                          CONHC.sub.4 H.sub.9                                                                         OH          O 177-179                                    559   CH.sub.3                                                                          CON(CH.sub.3)C.sub.4 H.sub.9                                                                OCH.sub.2 CHCH.sub.2                                                                       O 1.5465                                     560   CH.sub.3                                                                          CON(CH.sub.3)C.sub.4 H.sub.9                                                                OH          O 162-166                                    561   CH.sub.3                                                                           ##STR312##  OCH.sub.2 CHCH.sub.2                                                                       O 218-220                                    562   CH.sub.3                                                                          COSC.sub.4 H.sub.9 -i                                                                       OH          O 130-133                                    563   CH.sub.3                                                                           ##STR313##  OH          O 158-163                                    564   CH.sub.3                                                                          COOCH.sub.2 CCC.sub.2 H.sub.5                                                               OCH.sub.2 OCH.sub.3                                                                        O 95-97                                      565   CH.sub.3                                                                          COOCH.sub.2 CH.sub.2 CCCH.sub.3                                                             OCH.sub.2 OCH.sub.3                                                                        O 140.5-143                                  566   CH.sub.3                                                                          COOCH.sub.2 CH.sub.2 CH.sub.2 CCH                                                           OCH.sub.2 OCH.sub.3                                                                        O 78-81                                      567   CH.sub.3                                                                          COOCH(CH.sub.3)CH.sub.2 CCH                                                                 OCH.sub.2 OCH.sub.3                                                                        O   137-138.5                                568   CH.sub.3                                                                          COOCH(C.sub.2 H.sub.5)CCH                                                                   OCH.sub.2 OCH.sub.3                                                                        O 138-140                                    569   CH.sub.3                                                                          COSCH.sub.2 CHCH.sub.2                                                                      OCH.sub.2 OCH.sub.3                                                                        O 1.5850                                     570   CH.sub.3                                                                          COOCH.sub.2 CCC.sub.2 H.sub.5                                                               OH          O 167-169                                    571   CH.sub.3                                                                          COOCH.sub.2 CH.sub.2 CCCH.sub.3                                                             OH          O Unmeasurable                               572   CH.sub.3                                                                          COOCH.sub.2 CH.sub.2 CH.sub.2 CCH                                                           OH          O   160-161.5                                573   CH.sub.3                                                                          COOCH(CH.sub.3)CH.sub.2 CCH                                                                 OH          O 133-135                                    574   CH.sub.3                                                                          COOCH(C.sub.2 H.sub.5)CCH                                                                   OH          O   155-156.5                                575   C.sub.2 H.sub.5                                                                   COOH         OH          O   171-174.5                                576   CH.sub.3                                                                          COOC.sub.3 H.sub.7                                                                          OCH(CH.sub.3)OCOC.sub.2 H.sub.5                                                            O 104.5-107                                  577   CH.sub.3                                                                          COOC.sub.3 H.sub.7                                                                          OCH(CH.sub.3)OCOC.sub.3 H.sub.7                                                            O   104-105.5                                578   CH.sub.3                                                                          COOC.sub.3 H.sub.7                                                                          OCH(CH.sub.3)OCOC.sub.3 H.sub.7 -i                                                         O 123-126                                    579   CH.sub.3                                                                          COOC.sub.3 H.sub.7                                                                          OCH(CH.sub.3)OCOC.sub.4 H.sub.9 -i                                                         O 124.5-126.5                                __________________________________________________________________________

                                      TABLE 36                                     __________________________________________________________________________     Compound                         m.p. (°C.)                             No.   R.sup.1                                                                           R.sup.2     R        X  or (n.sub.D.sup.20)                           __________________________________________________________________________     580   CH.sub.3                                                                           ##STR314## OCH.sub.2 CHCH.sub.2                                                                    O  97-99                                         581   CH.sub.3                                                                           ##STR315## OH       O  110-114                                       582   CH.sub.3                                                                          COOCH.sub.2 CH.sub.2 Cl                                                                    OCH.sub.2 CHCH.sub.2                                                                    O   99-101                                       583   CH.sub.3                                                                          COOCH.sub.2 CHCl.sub.2                                                                     OCH.sub.2 CHCH.sub.2                                                                    O  97-98                                         584   CH.sub.3                                                                          COOCH.sub.2 CCl.sub.3                                                                      OCH.sub.2 CHCH.sub.2                                                                    O    126-128.5                                   585   CH.sub.3                                                                          COOCH.sub.2 CH.sub.2 Cl                                                                    OH       O  155-157                                       586   CH.sub.3                                                                          COOCH.sub.2 CHCl.sub.2                                                                     OH       O  129-132                                       587   CH.sub.3                                                                          COOCH.sub.2 CCl.sub.3                                                                      OH       O   97-101                                       588   CH.sub.3                                                                          COOCH.sub.2 CH.sub.2 Br                                                                    OCH.sub.2 CHCH.sub.2                                                                    O  106-108                                       589   CH.sub.3                                                                          COOCH.sub.2 CH.sub.2 CN                                                                    OCH.sub.2 CHCH.sub.2                                                                    O  128-130                                       590   CH.sub.3                                                                          COOCH.sub.2 CH.sub.2 Br                                                                    OH       O  159-162                                       591   CH.sub.3                                                                          COOCH.sub.2 CH.sub.2 CN                                                                    OH       O    177-179.5                                   592   CH.sub.3                                                                          COOCH(CF.sub.3).sub.2                                                                      OCH.sub.2 CHCH.sub.2                                                                    O  139-141                                       593   CH.sub.3                                                                           ##STR316## OCH.sub.2 CHCH.sub.2                                                                    O  85-89                                         594   CH.sub.3                                                                           ##STR317## OCH.sub.2 CHCH.sub.2                                                                    O    98-101.5                                    595   CH.sub.3                                                                           ##STR318## OH       O  160-162                                       596   CH.sub.3                                                                           ##STR319## OH       O  155-158                                       597   CH.sub.3                                                                          COSCH.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                    OCH.sub.2 CHCH.sub.2                                                                    O  72-74                                         598   CH.sub.3                                                                          COSCH.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                    OH       O   99-101                                       599   CH.sub.3                                                                          COSCH.sub.2 CH.sub.2 N(C.sub.2 H.sub.5).sub.2                                              OCH.sub.2 CHCH.sub.2                                                                    O    68-69.5                                     600   CH.sub.3                                                                          COSCH.sub.2 CH.sub.2 N(C.sub.2 H.sub.5).sub.2                                              OH       O  139-142                                       601   H                                                                                  ##STR320## OH       O  158-163                                       602   C.sub.2 H.sub.5                                                                    ##STR321##                                                                                 ##STR322##                                                                             O  110-112                                       __________________________________________________________________________

                                      TABLE 37                                     __________________________________________________________________________     Compound                         m.p. (°C.)                             No.   R.sup.1                                                                            R.sup.2   R        X   or (n.sub.D.sup.20)                           __________________________________________________________________________     603   C.sub.2 H.sub.5                                                                    COC.sub.2 H.sub.5                                                                        OH       O   140.5-143                                     604   C.sub.4 H.sub.9                                                                    COCH.sub.3                                                                               OH       O   134-136                                       605   H                                                                                   ##STR323##                                                                              OCH.sub.2 CHCH.sub.2                                                                    O   100-103                                       606   CH.sub.3                                                                           H         OCH.sub.2 CHCH.sub.2                                                                    S   89-91                                         607   CH.sub.3                                                                           H         OH       S   151-155                                       608   CH.sub.3                                                                           COOC.sub.2 H.sub.5                                                                        ##STR324##                                                                             NCH.sub.3                                                                          151-156                                       609   CH.sub.3                                                                           COOC.sub.2 H.sub.5                                                                       OH       NCH.sub.3                                                                          200-202                                       610   CH.sub.3                                                                           COOC.sub.4 H.sub.9 -t                                                                     ##STR325##                                                                             NH  183-187                                       611   CH.sub.3                                                                           COOC.sub.4 H.sub.9 -t                                                                    OH       NH  187-190                                       612   CH.sub.3                                                                           H         OH       NH  167-170                                       613   CH.sub.3                                                                           COOCH.sub.3                                                                               ##STR326##                                                                             NH  164-166                                       614   CH.sub.3                                                                           COOCH.sub.3                                                                              OH       NH  194-197                                       615   CH.sub.3                                                                           COOCH.sub.2 CHCH.sub.2                                                                    ##STR327##                                                                             NH  204-208                                       616   CH.sub.3                                                                           COOH                                                                                      ##STR328##                                                                             NH  161-164                                       617   CH.sub.3                                                                           COOC.sub.3 H.sub.7                                                                       OH       NH  175-179                                       618   CH.sub.3                                                                           COOC.sub.3 H.sub.7 -i                                                                    OH       NH  180-183                                       619   CH.sub.3                                                                           COOC.sub.4 H.sub.9                                                                       OH       NH  143-148                                       620   CH.sub.3                                                                           COOC.sub.4 H.sub.9 -i                                                                    OH       NH    140-146.5                                   621   CH.sub.3                                                                           COOC.sub.4 H.sub.9 -s                                                                    OH       NH  145-150                                       622   CH.sub.3                                                                           COOC.sub.5 H.sub.11                                                                      OH       NH  119-123                                       623   CH.sub.3                                                                           COOC.sub.6 H.sub.13                                                                      OH       NH  125-130                                       624   CH.sub.3                                                                           COOC.sub.3 H.sub.7                                                                        ##STR329##                                                                             NH  207-209                                       __________________________________________________________________________

                                      TABLE 38                                     __________________________________________________________________________     Compound                         m.p. (°C.)                             No.   R.sup.1                                                                            R.sup.2   R        X   or (n.sub.D.sup.20)                           __________________________________________________________________________     625   CH.sub.3                                                                           COOC.sub.3 H.sub.7 -i                                                                     ##STR330##                                                                             NH  203-205                                       626   CH.sub.3                                                                           COOC.sub.4 H.sub.9                                                                        ##STR331##                                                                             NH  191.5-194                                     627   CH.sub.3                                                                           COOC.sub.4 H.sub.9 -i                                                                     ##STR332##                                                                             NH  200-203                                       628   CH.sub.3                                                                           COOC.sub.4 H.sub.9 -s                                                                     ##STR333##                                                                             NH  170-173                                       629   CH.sub.3                                                                           COOC.sub.5 H.sub.11                                                                       ##STR334##                                                                             NH  137-139                                       630   CH.sub.3                                                                           COOC.sub.6 H.sub.13                                                                       ##STR335##                                                                             NH  130-133                                       631   CH.sub.3                                                                            ##STR336##                                                                               ##STR337##                                                                             NH  181-184                                       632   CH.sub.3                                                                            ##STR338##                                                                               ##STR339##                                                                             NH  192.5-196                                     633   CH.sub.3                                                                           COOCH.sub.2 CH.sub.2 OCH.sub.3                                                            ##STR340##                                                                             NH  187-190                                       634   CH.sub.3                                                                           COCF.sub.3                                                                               OH       NH  162-167                                       635   CH.sub.3                                                                           COCF.sub.3                                                                                ##STR341##                                                                             NH  165-167                                       636   CH.sub.3                                                                            ##STR342##                                                                              OH       NH  223-227                                       637   CH.sub.3                                                                           COOCH.sub.2 CH.sub.2 OCH.sub.3                                                           OH       NH  182-186                                       638   CH.sub.3                                                                           Cl        OH       NH  176-179                                       639   CH.sub.3                                                                           COC.sub.2 H.sub.5                                                                        OH       NH  192-195                                       640   CH.sub.3                                                                           COC.sub.2 H.sub.5                                                                         ##STR343##                                                                             NH  173-176                                       641   CH.sub.3                                                                           CN                                                                                        ##STR344##                                                                             NH  151-154                                       __________________________________________________________________________

                                      TABLE 39                                     __________________________________________________________________________     Compound                         m.p. (°C.)                             No.   R.sup.1                                                                           R.sup.2    R         X  or (n.sub.D.sup.20)                           __________________________________________________________________________     642   CH.sub.3                                                                          COCH.sub.3 OH        NH 198-203                                       643   CH.sub.3                                                                          COCH.sub.3                                                                                 ##STR345##                                                                              NH 206-211                                       644   CH.sub.3                                                                          CN                                                                                         ##STR346##                                                                              O  156-158                                       645   CH.sub.3                                                                          Br         OH        S  178-180                                       646   CH.sub.3                                                                          Br         OCH.sub.2 C(Br)CH.sub.2                                                                  S  126-128                                       647   CH.sub.3                                                                          Br         OCH.sub.2 CHCH.sub.2                                                                     S                                                648   CH.sub.3                                                                          COC.sub.3 H.sub.7                                                                          ##STR347##                                                                              NH                                               649   CH.sub.3                                                                          COC.sub.3 H.sub.7                                                                         OH        NH 193-196                                       650   CH.sub.3                                                                          CH.sub.2 CHCH.sub.2                                                                       OH        NH 130-134                                       651   CH.sub.3                                                                          C.sub.3 H.sub.7                                                                           OH        NH 137-142                                       652   CH.sub.3                                                                          COOCH.sub.2 CH.sub.2 F                                                                    OH        NH 193-195                                       653   CH.sub.3                                                                          COOCH.sub.2 CH.sub.2 Cl                                                                   OH        NH 203-205                                       654   CH.sub.3                                                                          COOCH(CH.sub.3)CH.sub.2 Cl                                                                OH        O  143-147                                       655   CH.sub.3                                                                          COOCH(CH.sub.2 Cl).sub.2                                                                  OH        O  115-119                                       656   CH.sub.3                                                                          COOCH(CH.sub.3)CH.sub.2 F                                                                 OH        O  150-153                                       657   CH.sub.3                                                                          COOCH(CH.sub.3)CF.sub.3                                                                   OH        O  125-128                                       658   CH.sub.3                                                                          COOCH.sub.2 CHF.sub.2                                                                     OH        O  144-147                                       659   CH.sub.3                                                                          COOCH.sub.2 CH.sub.2 CH.sub.2 F                                                           OH        O  153-156                                       660   CH.sub.3                                                                          COOCH.sub.2 CH.sub.2 OH                                                                   OH        O  148-151                                       661   CH.sub.3                                                                          COOCH.sub.2 COOC.sub.2 H.sub.5                                                            OH        O  130-133                                       662   CH.sub.3                                                                           ##STR348##                                                                               OH        O  154-157                                       663   CH.sub.3                                                                          CON(C.sub.2 H.sub.5).sub.2                                                                OH        NH 151-155                                       __________________________________________________________________________

                                      TABLE 40                                     __________________________________________________________________________      ##STR349##                                                                    Compound                          m.p. (°C.)                            No.   R.sup.2    R        X  W Z  or (n.sub.D.sup.20)                          __________________________________________________________________________     664   H                                                                                          ##STR350##                                                                             NH O CH 135-139                                      665   H          OH       NH O CH 167-170                                      666   CH.sub.2 CHCH.sub.2                                                                       OCH.sub.3                                                                               NH O CH                                              667   CH.sub.2 CHCH.sub.2                                                                       OH       NH O CH 130-134                                      668   CH.sub.2 CCH                                                                              OCH3     NH O CH                                              669   CH.sub.2 CCH                                                                              OH       NH O CH                                              670   CH.sub.2 CN                                                                               OCH3     NH O CH                                              671   CH.sub.2 CN                                                                               OH       NH O CH 165-169                                      672   CH.sub.2 COOCH.sub.3                                                                       ##STR351##                                                                             NH O CH                                              673   CH.sub.2 COOCH.sub.3                                                                      OH       NH O CH                                              674   CH.sub.2 N(CH.sub.3).sub.2                                                                OCH.sub.2 CHCH.sub.2                                                                    NH O CH                                              675   CH.sub.2 N(CH.sub.3).sub.2                                                                OH       NH O CH                                              676   CHCHCN     OCH.sub.2 CHCH.sub.2                                                                    NH O CH                                              677   CHCHCN     OH       NH O CH                                              678   CHCHNO.sub.2                                                                              OCH.sub.2 CHCH.sub.2                                                                    NH O CH                                              679   CHCHNO.sub.2                                                                              OH       NH O CH                                              680   CHO                                                                                        ##STR352##                                                                             NH O CH 148-149                                      681   CHO        OH       NH O CH 201-206                                      682   CHNC.sub.3 H.sub.7 -i                                                                     OCH.sub.2 CHCH.sub.2                                                                    NH O CH                                              683   CHNC.sub.3 H.sub.7 -i                                                                     OH       NH O CH                                              684                                                                                   ##STR353##                                                                               OCH.sub.2 CHCH.sub.2                                                                    NH O CH                                              __________________________________________________________________________

                                      TABLE 41                                     __________________________________________________________________________     Compound                                  m.p. (°C.)                    No.   R.sup.2       R             X  W Z  or (n.sub.D.sup.20)                  __________________________________________________________________________     685                                                                                   ##STR354##   OH            NH O CH                                      686                                                                                   ##STR355##                                                                                   ##STR356##   NH O CH                                      687                                                                                   ##STR357##   OH            NH O CH                                      688   CHNN(CH.sub.3).sub.2                                                                          ##STR358##   NH O CH                                      689   CHNN(CH.sub.3).sub.2                                                                         OH            NH O CH                                      690   CHNOH                                                                                         ##STR359##   NH O CH                                      691   CHNOH         OH            NH O CH 165-170                              692   CHNOCH.sub.3                                                                                  ##STR360##   NH O CH 131-133                              693   CHNOCH.sub.3  OH            NH O CH 171-175                              694   H             OH            NH O N  152-154                              695   CHNOCH.sub.3  OH            NH O N                                       696   CHNOCH.sub.3  OCH.sub.3     NH S CH                                      697   CHNOCH.sub.3  OH            NH S CH                                      698   CHNOCH.sub.3  OCH.sub.2 CCH NH O CH                                      699   CHNOCH.sub.3  OCH.sub.2 OCH.sub.3                                                                          NH O CH                                      700   CHNOCH.sub.3  OCH(CH.sub.3)OC(O)C.sub.4 H.sub.9 -t                                                         NH O CH                                      701   CHNOCH.sub.3                                                                                  ##STR361##   NH O CH                                      702   CHNOCH.sub.3  ONC(CH.sub.3).sub.2                                                                          NH O CH                                      703   CHNOCH.sub.3  SCH.sub.3     NH O CH                                      704   CHNOCH.sub.3  SCH.sub.2 CHCH.sub.2                                                                         NH O CH                                      705   CHNOCH.sub.3  SCH.sub.2 CCH NH O CH                                      __________________________________________________________________________

                                      TABLE 42                                     __________________________________________________________________________     Compound                             m.p. (°C.)                         No.   R.sup.1       R        X  W Z  or (n.sub.D.sup.20)                       __________________________________________________________________________     706   CHNOCH.sub.3                                                                                  ##STR362##                                                                             NH O CH                                           707   CHNOCH.sub.3  NHC.sub.2 H.sub.5                                                                       NH O CH                                           708   CHNOCH.sub.3                                                                                  ##STR363##                                                                             NH O CH                                           709   CHNOCH.sub.3  NHSO.sub.2 CH.sub.3                                                                     NH O CH                                           710   CHNOCH.sub.3                                                                                  ##STR364##                                                                             NH O CH                                           711   CHNOCH.sub.3                                                                                  ##STR365##                                                                             NH O CH                                           712   CHNOCH.sub.3                                                                                  ##STR366##                                                                             NH O CH                                           713   CHNOC.sub.3 H.sub.7 -i                                                                        ##STR367##                                                                             NH O CH                                           714   CHNOC.sub.3 H.sub.7 -i                                                                       OH       NH O CH 123-127                                   715   CHNOCH.sub.2 CHCH.sub.2                                                                      OH       NH O CH                                           716   CHNOCH.sub.2 CCH                                                                             OH       NH O CH                                           717                                                                                   ##STR368##   OCH.sub.2 CHCH.sub.2                                                                    NH O CH                                           718                                                                                   ##STR369##   OH       NH O CH                                           719                                                                                   ##STR370##   OCH.sub.3                                                                               NH O CH                                           720                                                                                   ##STR371##   OH       NH O CH                                           721   COOC.sub.2 H.sub.5                                                                            ##STR372##                                                                             NH O CH 196-199                                   722   NH.sub.2      OCH.sub.2 CHCH.sub.2                                                                    NH O CH 132-135                                   __________________________________________________________________________

                                      TABLE 43                                     __________________________________________________________________________     Compound                          m.p. (°C.)                            No.   R.sup.2    R        X  W Z  or (n.sub.D.sup.20)                          __________________________________________________________________________     723   NH.sub.2                                                                                   ##STR373##                                                                             NH O CH                                              724   NH.sub.2   OH       NH O CH                                              725   NHCH.sub.3                                                                                 ##STR374##                                                                             NH O CH                                              726   NHCH.sub.3 OH       NH O CH                                              727                                                                                   ##STR375##                                                                               OCH.sub.2 CHCH.sub.2                                                                    NH O CH                                              728                                                                                   ##STR376##                                                                               OH       NH O CH                                              729                                                                                   ##STR377##                                                                               OCH.sub.2 CHCH.sub.2                                                                    NH O CH                                              730                                                                                   ##STR378##                                                                               OH       NH O CH                                              731   N(CH.sub.3).sub.2                                                                          ##STR379##                                                                             NH O CH                                              732   N(CH.sub.3).sub.2                                                                         OH       NH O CH                                              733                                                                                   ##STR380##                                                                                ##STR381##                                                                             NH O CH                                              734                                                                                   ##STR382##                                                                               OH       NH O CH                                              735   NHC(O)CH.sub.3                                                                            OCH.sub.2 CHCH.sub.2                                                                    NH O CH 177-180                                      736   NHC(O)CH.sub.3                                                                            OH       NH O CH 230-233                                      737                                                                                   ##STR383##                                                                               OCH.sub.2 CHCH.sub.2                                                                    NH O CH                                              738                                                                                   ##STR384##                                                                               OH       NH O CH 168-172                                      739   NHCOOC.sub.2 H.sub.5                                                                      OCH.sub.2 CHCH.sub.2                                                                    NH O CH                                              740   NHCOOC.sub.2 H.sub.5                                                                      OH       NH O CH 177-179                                      __________________________________________________________________________

                                      TABLE 44                                     __________________________________________________________________________     Compound                             m.p. (°C.)                         No.   R.sup.2       R        X  W Z  or (n.sub.D.sup.20)                       __________________________________________________________________________     741   NHC(O)SC.sub.2 H.sub.5                                                                       OCH.sub.2 CHCH.sub.2                                                                    NH O CH                                           742   NHC(O)SC.sub.2 H.sub.5                                                                       OH       NH O CH                                           743                                                                                   ##STR385##   OCH.sub.2 CHCH.sub.2                                                                    NH O CH                                           744                                                                                   ##STR386##   OH       NH O CH                                           745   NHC(O)NHCH.sub.3                                                                             OCH.sub.2 CHCH.sub.2                                                                    NH O CH                                           746   NHC(O)NHCH.sub.3                                                                             OH       NH O CH                                           747   NHC(O)N(CH.sub.3).sub.2                                                                       ##STR387##                                                                             NH O CH                                           748   NHC(O)N(CH.sub.3).sub.2                                                                      OH       NH O CH                                           749   NHSO.sub.2 CH.sub.3                                                                          OCH.sub.2 CHCH.sub.2                                                                    NH O CH                                           750   NHSO.sub.2 CH.sub.3                                                                          OH       NH O CH                                           751                                                                                   ##STR388##   OCH.sub.2 CHCH.sub.2                                                                    NH O CH                                           752                                                                                   ##STR389##   OH       NH O CH                                           753   NCHCH.sub.3   OCH.sub.2 CHCH.sub.2                                                                    NH O CH                                           754   NCHCH.sub.3   OH       NH O CH                                           755                                                                                   ##STR390##   OCH.sub.2 CHCH.sub.2                                                                    NH O CH                                           756                                                                                   ##STR391##   OH       NH O CH 265-270                                   757                                                                                   ##STR392##   OCH.sub.2 CHCH.sub.2                                                                    NH O CH                                           758                                                                                   ##STR393##   OH       NH O CH                                           759   NO.sub.2      OCH.sub.2 CHCH.sub.2                                                                    NH O CH 155-159                                   760   NO.sub.2      OH       NH O CH >300° C.                           __________________________________________________________________________

                                      TABLE 45                                     __________________________________________________________________________     Compound                                m.p. (°C.)                      No.   R.sup.2                                                                              R        X          W    Z  or (n.sub.D.sup.20)                    __________________________________________________________________________     761   NO.sub.2                                                                             OCH.sub.2 CHCH.sub.2                                                                    NCH.sub.3  O    CH                                        762   NO.sub.2                                                                             OH       NCH.sub.3  O    CH                                        763   COOC.sub.2 H.sub.5                                                                    ##STR394##                                                                             NCH.sub.2 CHCH.sub.2                                                                      O    CH 1.5774                                 764   COOC.sub.2 H.sub.5                                                                   OH       NCH.sub.2 CHCH.sub.2                                                                      O    CH                                        765   NH.sub.2                                                                              ##STR395##                                                                             NCH.sub.2 CHCH.sub.2                                                                      O    CH                                        766   NH.sub.2                                                                             OH       NCH.sub.2 CHCH.sub.2                                                                      O    CH 215-220                                767   H     OCH.sub.2 OCH.sub.3                                                                     NCH.sub.2 CCH                                                                             O    CH                                        768   H     OH       NCH.sub.2 CCH                                                                             O    CH                                        769   COOC.sub.2 H.sub.5                                                                   OCH.sub.3                                                                               NCH.sub.2 OCH.sub.3                                                                       O    CH                                        770   COOC.sub.2 H.sub.5                                                                   OH       NCH.sub.2 OCH.sub.3                                                                       O    CH 158-162                                771   COOC.sub.2 H.sub.5                                                                    ##STR396##                                                                             NCH.sub.2 OC(O)C.sub.4 H.sub.9 -t                                                         O    CH   182-183.5                            772   COOC.sub.2 H.sub.5                                                                   OH       NCH.sub.2 OC(O)C.sub.4 H.sub.9 -t                                                         O    CH 193-195                                773   COOC.sub.2 H.sub.5                                                                    ##STR397##                                                                             NCH.sub.2 COOC.sub.2 H.sub.5                                                              O    CH   141-143.5                            774   COOC.sub.2 H.sub.5                                                                   OH       NCH.sub.2 COOC.sub.2 H.sub.5                                                              O    CH 190-193                                775   H     OH       NC(O)CH.sub.3                                                                             O    CH                                        776   H     OH       NC(O)CH.sub.3                                                                             CH.sub.2                                                                            CH                                        777   H     OH       NC(O)CH.sub.3                                                                             CH(CN)                                                                              CH                                        778   H     OH       NC(O)CH.sub.3                                                                             C(O) CH                                        779   H     OCH.sub.3                                                                               NC(O)CH.sub.3                                                                             N(CHO)                                                                              CH                                        780   Cl    OCH.sub.2 OCH.sub.3                                                                     NC(O)CH.sub.3                                                                             O    CH                                        781   Cl    OH       NC(O)CH.sub.3                                                                             O    CH                                        782   OCH.sub.3                                                                             ##STR398##                                                                             NC(O)CH.sub.3                                                                             O    CH                                        __________________________________________________________________________

                                      TABLE 46                                     __________________________________________________________________________     Compound                                m.p. (°C.)                      No.   R.sup.2   R        X         W Z  or (n.sub.D.sup.20)                    __________________________________________________________________________     783   OCH.sub.3 OH       NC(O)CH.sub.3                                                                            O CH                                        784                                                                                   ##STR399##                                                                              OCH.sub.2 CHCH.sub.2                                                                    NC(O)CH.sub.3                                                                            O CH                                        785                                                                                   ##STR400##                                                                              OH       NC(O)CH.sub.3                                                                            O CH                                        786   COOCH.sub.3                                                                               ##STR401##                                                                             NC(O)CH.sub.3                                                                            O CH 133-135                                787   COOCH.sub.3                                                                              OH       NC(O)CH.sub.3                                                                            O CH 186-189                                788   COOC.sub.2 H.sub.5                                                                        ##STR402##                                                                             NC(O)CH.sub.3                                                                            O CH   128-130.5                            789   COOC.sub.2 H.sub.5                                                                       OH       NC(O)CH.sub.3                                                                            O CH 174-177                                790   COOCH.sub.2 CHCH.sub.2                                                                   OC.sub.2 H.sub.4 Si(CH.sub.3).sub.3                                                     NC(O)CH.sub.3                                                                            O CH                                        791   COOCH.sub.2 CHCH.sub.2                                                                   OH       NC(O)CH.sub.3                                                                            O CH                                        792   COOCH.sub.2 CCH                                                                          OCH.sub.2 OCH.sub.3                                                                     NC(O)CH.sub.3                                                                            O CH                                        793   COOCH.sub.2 CCH                                                                          OH       NC(O)CH.sub.3                                                                            O CH                                        794   C(O)SCH.sub.3                                                                            OCH.sub.3                                                                               NC(O)CH.sub.3                                                                            O CH                                        795   C(O)SCH.sub.3                                                                            OH       NC(O)CH.sub.3                                                                            O CH                                        796   COOC.sub.2 H.sub.5                                                                        ##STR403##                                                                              ##STR404##                                                                              O CH   128-132.5                            797   COOC.sub.2 H.sub.5                                                                       OH                                                                                       ##STR405##                                                                              O CH 113-115                                798                                                                                   ##STR406##                                                                              OCH.sub.2 OCH.sub.3                                                                      ##STR407##                                                                              O CH                                        799                                                                                   ##STR408##                                                                              OH                                                                                       ##STR409##                                                                              O CH                                        __________________________________________________________________________

                                      TABLE 47                                     __________________________________________________________________________     Compound                                     m.p. (°C.)                 No.   R.sup.2     R        X            W Z  or (n.sub.D.sup.20)               __________________________________________________________________________     800                                                                                   ##STR410##                                                                                 ##STR411##                                                                              ##STR412##  O CH                                   801                                                                                   ##STR413## OH                                                                                       ##STR414##  O CH                                   802   C(O)SCH.sub.2 CHCH.sub.2                                                                   OCH.sub.2 CHCH.sub.2                                                                     ##STR415##  O CH                                   803   C(O)SCH.sub.2 CHCH.sub.2                                                                   OH                                                                                       ##STR416##  O CH                                   804   C(O)SCH.sub.2 CCH                                                                          OCH.sub.2 CHCH.sub.2                                                                     ##STR417##  O CH                                   805   C(O)SCH.sub.2 CCH                                                                          OH                                                                                       ##STR418##  O CH                                   806   C(O)CH.sub.3                                                                                ##STR419##                                                                              ##STR420##  O CH                                   807   C(O)CH.sub.3                                                                               OH                                                                                       ##STR421##  O CH                                   808                                                                                   ##STR422## OH                                                                                       ##STR423##  O CH                                   809                                                                                   ##STR424## OH                                                                                       ##STR425##  O CH                                   810                                                                                   ##STR426## OH                                                                                       ##STR427##  O CH                                   811   H           OH                                                                                       ##STR428##  O CH                                   812   COOC.sub.2 H.sub.5                                                                          ##STR429##                                                                             NCOOC.sub.2 H.sub.5                                                                         O CH 105-108                           813   COOC.sub.2 H.sub.5                                                                         OH       NCOOC.sub.2 H.sub.5                                                                         O CH 170-173                           814   COOC.sub.2 H.sub.5                                                                          ##STR430##                                                                             NCOOC.sub.4 H.sub.9 -t                                                                      O CH 1.5649                            815   COOC.sub.2 H.sub.5                                                                         OH       NCOOC.sub.4 H.sub.9 -t                                                                      O CH 138-142                           __________________________________________________________________________

                                      TABLE 48                                     __________________________________________________________________________     Compound                               m.p. (°C.)                       No.   R.sup.2                                                                              R        X            W Z  or (n.sub.D.sup.20)                     __________________________________________________________________________     816   H     OCH.sub.2 CHCH.sub.2                                                                     ##STR431##  O CH                                         817   H     OH                                                                                       ##STR432##  O CH                                         818   H                                                                                     ##STR433##                                                                              ##STR434##  O CH                                         819   H     OH                                                                                       ##STR435##  O CH                                         820   H     OCH.sub.2 CHCH.sub.2                                                                    NC(O)SCH.sub.3                                                                              O CH                                         821   H     OH       NC(O)SCH.sub.3                                                                              O CH                                         822   H     OCH.sub.2 CHCH.sub.2                                                                     ##STR436##  O CH                                         823   H     OH                                                                                       ##STR437##  O CH                                         824   COOC.sub.2 H.sub.5                                                                    ##STR438##                                                                             NC(O)N(CH.sub.3).sub.2                                                                      O CH 1.5767                                  825   COOC.sub.2 H.sub.5                                                                   OH       NC(O)N(CH.sub.3).sub.2                                                                      O CH 172-174                                 826   COOC.sub.2 H.sub.5                                                                    ##STR439##                                                                             NSO.sub.2 CH.sub.3                                                                          O CH 140.5-145                               827   COOC.sub.2 H.sub.5                                                                   OH       NSO.sub.2 CH.sub.3                                                                          O CH 186-188                                 828   COOC.sub.2 H.sub.5                                                                    ##STR440##                                                                              ##STR441##  O CH Unmeasurable                            829   COOC.sub.2 H.sub.5                                                                   OH                                                                                       ##STR442##  O CH 149-152                                 830   COOC.sub.2 H.sub.5                                                                    ##STR443##                                                                             NSi(CH.sub.3).sub.2 C.sub.4 H.sub.9 -t                                                      O CH Unmeasurable                            831   COOC.sub.2 H.sub.5                                                                   OH       NSi(CH.sub.3).sub.2 C.sub.4 H.sub.9 -t                                                      O CH 175-178                                 832   COOC.sub.2 H.sub.5                                                                    ##STR444##                                                                             NSCCl.sub.3  O CH 173-177                                 __________________________________________________________________________

                                      TABLE 49                                     __________________________________________________________________________     Compound                            m.p. (°C.)                          No.   R.sup.2                                                                              R        X         W Z  or (n.sub.D.sup.20)                        __________________________________________________________________________     833   COOC.sub.2 H.sub.5                                                                   OH       NSCCl.sub.3                                                                              O CH                                            834   H     OCH.sub.3                                                                                ##STR445##                                                                              O CH 187-190                                    835   H     OH                                                                                       ##STR446##                                                                              O CH   182-183.5                                836   CN                                                                                    ##STR447##                                                                              ##STR448##                                                                              O CH 176-177                                    837   H                                                                                     ##STR449##                                                                             NC(O)CH.sub.3                                                                            O CH                                            838   H     OH       NC(O)CH.sub.3                                                                            O CH                                            839   H     OCH.sub.2 CHCH.sub.2                                                                    NC(O)CH.sub.3                                                                            O CH                                            840   H     OH       NC(O)CH.sub.3                                                                            O CH                                            841   H     OH       NC(O)CH.sub.3                                                                            O CH                                            __________________________________________________________________________

                                      TABLE 50                                     __________________________________________________________________________      ##STR450##                                                                    Compound                                 m.p. (°C.)                     No.   R.sup.1                                                                           R.sup.2 R.sup.3                                                                             R.sup.4                                                                            R  X      W Z  or (n.sub.D.sup.20)                   __________________________________________________________________________     842   CH.sub.3                                                                          H       CH.sub.3                                                                            CH.sub.3                                                                           OH NH     O CH 184-186                               843   CH.sub.3                                                                          CHNOCH.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                                                                           OH NH     O CH                                       844   CH.sub.3                                                                          H       N(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OH NH     O CH 164-167                               845   CH.sub.3                                                                          H       NHCH.sub.3                                                                          OCH.sub.3                                                                          OH NC(O)CH.sub.3                                                                         O CH                                       846   CF.sub.3                                                                          H       OCH.sub.3                                                                           OCH.sub.3                                                                          OH NC(O)CH.sub.3                                                                         O CH                                       __________________________________________________________________________

                                      TABLE 51                                     __________________________________________________________________________      ##STR451##                                                                    Compound                             m.p. (°C.)                         No.   X.sup.1                                                                           Q.sup.1      X.sup.2                                                                               R       or (n.sub.D.sup.20)                       __________________________________________________________________________     847   CH.sub.2                                                                          CH.sub.2     CO     OCH.sub.3                                                                              150-153                                   848   CH.sub.2                                                                          CH.sub.2     CO     OH      181.5-184                                 849   CH.sub.2                                                                          CH.sub.2     CNOCH.sub.3                                                                           OCH.sub.3                                                                              152-154                                   850   CH.sub.2                                                                          CH.sub.2     CNOCH.sub.3                                                                           OH                                                851   CH.sub.2                                                                          CH.sub.2     CHOH   OCH.sub.3                                                                              135-137                                   852   CH.sub.2                                                                          CH.sub.2     CHOH   OH        151-153.5                               853   NH CO           O      OC.sub.2 H.sub.4 Si(CH.sub.3).sub.3                                                    Unmeasurable                              854   NH CO           O      OH      188-189                                   855   NH CO           NH     OCH.sub.3                                         856   NH CO           NH     OH                                                857   NH CC(CN)COOCH.sub.3                                                                           O      OC.sub.2 H.sub.4 Si(CH.sub.3).sub.3                                                    100-105                                   858   NH CC(CN)COOCH.sub.3                                                                           O      OH      250-260                                   859   NH CC(CN).sub.2 O      OC.sub.2 H.sub.4 Si(CH.sub.3).sub.3                                                    185-187                                   860   NH CC(CH).sub.2 O      O.sup.- N.sup.+ (C.sub.4 H.sub.9).sub.4                                                125-130                                   861   NH                                                                                 ##STR452##  O      OC.sub.2 H.sub.4 Si(CH.sub.3).sub.3               862   NH                                                                                 ##STR453##  O      OH                                                863   NH                                                                                 ##STR454##  O      OC.sub.2 H.sub.4 Si(CH.sub.3).sub.3               864   NH                                                                                 ##STR455##  O      OH                                                865   O  CO           S      OCH.sub.3                                                                              138-139                                   866   O  CO           S      OH                                                __________________________________________________________________________

                                      TABLE 52                                     __________________________________________________________________________      ##STR456##                                                                    Compound                              m.p. (°C.)                        No.   X.sup.1                                                                            Q.sup.2                                                                             Q.sup.3                                                                              X.sup.2                                                                               R         or (n.sub.D.sup.20)                      __________________________________________________________________________     867   CH.sub.2                                                                           CH.sub.2                                                                            CH.sub.2                                                                             CO     OCH.sub.3 185-187                                  868   CH.sub.2                                                                           CH.sub.2                                                                            CH.sub.2                                                                             CO     OH        183-189                                  869   CH.sub.2                                                                           CH.sub.2                                                                            CH.sub.2                                                                             CNOCH.sub.3                                                                           OCH.sub.3 128-131                                  870   CH.sub.2                                                                           CH.sub.2                                                                            CH.sub.2                                                                             CNOCH.sub.3                                                                           OH                                                 871   CH.sub.2                                                                           CH.sub.2                                                                            CH.sub.2                                                                             CHOH   OCH.sub.3                                          872   CH.sub.2                                                                           CH.sub.2                                                                            CH.sub.2                                                                             CHOH   OH        147.5-149                                873   CH.sub.2                                                                           CH.sub.2                                                                            CH.sub.2                                                                             CH.sub.2                                                                               ##STR457##                                                                              1.5332                                   874   CH.sub.2                                                                           CH.sub.2                                                                            CH.sub.2                                                                             CH.sub.2                                                                              OCH.sub.3 127-128                                  875   CH.sub.2                                                                           CH.sub.2                                                                            CH.sub.2                                                                             CH.sub.2                                                                              OH        141-147                                  876   CH.sub.2                                                                           CH.sub.2                                                                            C(CH.sub.3).sub.2                                                                    O      OCH.sub.3                                          877   CH.sub.2                                                                           CH.sub.2                                                                            C(CH.sub.3).sub.2                                                                    O      OH        151-153                                  878   NH  CO   CH.sub.2                                                                             O      OC.sub.2 H.sub.4 Si(CH.sub.3).sub.3                                                      148-150                                  879   NH  CO   CH.sub.2                                                                             O      OH        200-202                                  880   NCH.sub.3                                                                          CO   CH.sub.2                                                                             O      OC.sub.2 H.sub.4 Si(CH.sub.3).sub.3                                                      Unmeasurable                             881   NCH.sub.3                                                                          CO   CH.sub.2                                                                             O      OH        178-180                                  882   NH  CO   CH(C.sub.2 H.sub.5)                                                                  O      OC.sub.2 H.sub.4 Si(CH.sub.3).sub.3                                                      Unmeasurable                             883   NH  CO   CH(C.sub.2 H.sub.5)                                                                  O      OH        195-197                                  884   NH  CH.sub.2                                                                            CH.sub.2                                                                             O      OC.sub.2 H.sub.4 Si(CH.sub.3).sub.3                                                      1.5333                                   885   NH  CH.sub.2                                                                            CH.sub.2                                                                             O      OH        160-164                                  886   NH  CH.sub.2                                                                            CH.sub.2                                                                             S      OC.sub.2 H.sub.4 Si(CH.sub.3).sub.3                                                      Unmeasurable                             887   NH  CH.sub.2                                                                            CH.sub.2                                                                             S      OH        164-166                                  888   NH  CH.sub.2                                                                            CH.sub.2                                                                             NH     OCH.sub.3                                          889   NH  CH.sub.2                                                                            CH.sub.2                                                                             NH     OH                                                 890   NH  CH(CH.sub.3)                                                                        CH.sub.2                                                                             O      OC.sub.2 H.sub.4 Si(CH.sub.3).sub.3                                                      Unmeasurable                             891   NH  CH(CH.sub.3)                                                                        CH.sub.2                                                                             O      OH        174-175                                  892   NH  CH.sub.2                                                                            CH(CH.sub.3)                                                                         O      OH        110-115                                  893   NH  CH.sub.2                                                                            CH(C.sub.2 H.sub.5)                                                                  O      OH                                                 __________________________________________________________________________

                                      TABLE 53                                     __________________________________________________________________________     Compound                        m.p. (°C.)                              No.   X.sup.1                                                                           Q.sup.2                                                                           Q.sup.3   X.sup.2                                                                          R       or (n.sub.D.sup.20)                            __________________________________________________________________________     894   NH CH.sub.2                                                                          C(CH.sub.3).sub.2                                                                        O OC.sub.2 H.sub.4 Si(CH.sub.3).sub.3                    895   NH CH.sub.2                                                                          C(CH.sub.3).sub.2                                                                        O OH                                                     896   NH CH.sub.2                                                                          C═CH.sub.2                                                                           O OC.sub.2 H.sub.4 Si(CH.sub.3).sub.3                                                    Unmeasurable                                   897   NH CH.sub.2                                                                          C═CH.sub.2                                                                           O OH      90-95                                          898   NH CH.sub.2                                                                          C═CHCH.sub.3                                                                         O OC.sub.2 H.sub.4 Si(CH.sub.3).sub.3                    899   NH CH.sub.2                                                                          C═CHCH.sub.3                                                                         O OH                                                     900   NH CH.sub.2                                                                          CH(CH.sub.2 COOCH.sub.3)                                                                 O OC.sub.2 H.sub.4 Si(CH.sub.3).sub.3                                                    Unmeasurable                                   901   NH CH.sub.2                                                                          CH(CH.sub.2 COOCH.sub.3)                                                                 O OH                                                     __________________________________________________________________________

                  TABLE 54                                                         ______________________________________                                          ##STR458##                                                                    Compound                                 m.p. (°C.)                     No.     a       b       d     e    R     or (n.sub.D.sup.20)                   ______________________________________                                         902     N       CH      CH    CH   H     159-161                               903     N       CH      CH    CH   OH    195-198                               904     N       CH      CH    CH   OCH.sub.3                                                                            160-162                               905     CH      N       CH    CH   H                                           906     CH      N       CH    CH   OH                                          907     CH      N       CH    CH   OCH.sub.3                                   908     CH      CH      N     CH   H                                           909     CH      CH      N     CH   OH                                          910     CH      CH      N     CH   OCH.sub.3                                   911     N       N       CH    CH   H                                           912     N       N       CH    CH   OH                                          913     N       N       CH    CH   OCH.sub.3                                   914     N       CH      N     CH   H                                           915     N       CH      N     CH   OH    174-177                               916     N       CH      N     CH   OCH.sub.3                                   917     N       CH      CH    N    H                                           918     N       CH      CH    N    OH    148-151                               919     N       CH      CH    N    OCH.sub.3                                                                            164-166                               920     CH      N       N     CH   H                                           921     CH      N       N     CH   OH                                          922     CH      N       N     CH   OCH.sub.3                                   923     CH      N       CH    N    H                                           924     CH      N       CH    N    OH                                          925     CH      N       CH    N    OCH.sub.3                                   926     CH      CH      N     N    H                                           927     CH      CH      N     N    OH                                          928     CH      CH      N     N    OCH.sub.3                                   ______________________________________                                    

                                      TABLE 55                                     __________________________________________________________________________      ##STR459##                                                                    Compound                              m.p. (°C.)                        No.   R.sup.1                                                                           R.sup.2       R         X    or (n.sub.D.sup.20)                      __________________________________________________________________________     929   CH.sub.3                                                                          COOCH(CH.sub.2 F).sub.2                                                                      OH        O    149-152                                  930   CH.sub.3                                                                          COOH          OCH.sub.2 OC.sub.2 H.sub.4 OCH.sub.3                                                     O    139-141                                  931   CH.sub.3                                                                          COOC.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                          OH        O    143.5-146                                932   CH.sub.3                                                                          COOC.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                          OCH.sub.2 CHCH.sub.2                                                                     O    92-94                                    933   CH.sub.3                                                                          COOCH.sub.2 CH(OCH.sub.3).sub.2                                                              OH        O    153-155                                  934   CH.sub.3                                                                          COOCH.sub.2 CH(OCH.sub.3).sub.2                                                              OCH.sub.2 CHCH.sub.2                                                                     O    75-77                                    935   CH.sub.3                                                                          COOCH.sub.2 C(CH.sub.3)CH.sub.2                                                              OH        O    143-146                                  936   CH.sub.3                                                                          COOCH.sub.2 C(CH.sub.3)CH.sub.2                                                              OCH.sub.2 OCH.sub.3                                                                      O     98-100                                  937   CH.sub.3                                                                          COOC.sub.2 H.sub.4 N(CH.sub.3).sub.2                                                         OH        O    194-197                                  938   CH.sub.3                                                                          COOCH.sub.2 CHC(CH.sub.3).sub.2                                                              OCH.sub.2 OCH.sub.3                                                                      O    96-98                                    939   CH.sub.3                                                                          COOCH(CH.sub.3)CHCHCH.sub.3                                                                  OCH.sub.2 OCH.sub.3                                                                      O    72-75                                    940   CH.sub.3                                                                          COOCH(CH.sub.3)CH.sub.2 Cl                                                                   OCH.sub.2 CHCH.sub.2                                                                     O    114-116                                  941   CH.sub.3                                                                          COOCH(CH.sub.2 Cl).sub.2                                                                     OCH.sub.2 CHCH.sub.2                                                                     O    138-140                                  942   CH.sub.3                                                                          COOCH(CH.sub.3)CH.sub.2 F                                                                    OCH.sub.2 CHCH.sub.2                                                                     O    104-107                                  943   CH.sub.3                                                                          COOCH(CH.sub.3)CF.sub.3                                                                      OCH.sub.2 CHCH.sub.2                                                                     O      118-119.5                              944   CH.sub.3                                                                          COOCH.sub.2 CHF.sub.2                                                                        OCH.sub.2 CHCH.sub.2                                                                     O    103-106                                  945   CH.sub.3                                                                          COOCH.sub.2 CH.sub.2 CH.sub.2 F                                                              OCH.sub.2 CHCH.sub.2                                                                     O    58-61                                    946   CH.sub.3                                                                          COOCH.sub.2 CH.sub.2 OH                                                                      OCH.sub.2 CHCH.sub.2                                                                     O    121-124                                  947   CH.sub.3                                                                          COOCH.sub.2 CO.sub.2 C.sub.2 H.sub.5                                                         OCH.sub.2 CHCH.sub.2                                                                     O    93-95                                    948   CH.sub.3                                                                           ##STR460##   OCH.sub.2 CHCH.sub.2                                                                     O    109-110                                  949   H  H             OH        NPym 190-193                                  950   H  H             OH        NH   169-170                                  951   CH.sub.3                                                                          CN                                                                                            ##STR461##                                                                              NH   169-172                                  __________________________________________________________________________      (In this Table, Pym indicates 4,6dimethoxypirimidin-2-yl.)               

                                      TABLE 56                                     __________________________________________________________________________     Compound                            m.p. (°C.)                          No.   R.sup.1                                                                           R.sup.2       R         X  or (n.sub.D.sup.20)                        __________________________________________________________________________     952   CH.sub.3                                                                          CN            OH        NH 185-189                                    953   CH.sub.3                                                                          CH.sub.2 CN                                                                                   ##STR462##                                                                              NH 151-156                                    954   CH.sub.3                                                                          COCOOC.sub.2 H.sub.5                                                                          ##STR463##                                                                              NH 150-153                                    955   CH.sub.3                                                                          COCOOC.sub.2 H.sub.5                                                                         OH        NH 179-183                                    956   CH.sub.3                                                                           ##STR464##                                                                                   ##STR465##                                                                              NH 82-85                                      957   CH.sub.3                                                                           ##STR466##   OH        NH 143-146                                    958   CH.sub.3                                                                           ##STR467##                                                                                   ##STR468##                                                                              NH 89-92                                      959   CH.sub.3                                                                           ##STR469##   OH        NH 127-129                                    960   CH.sub.3                                                                           ##STR470##                                                                                   ##STR471##                                                                              NH 94-99                                      961   CH.sub.3                                                                           ##STR472##   OH        NH 137-140                                    962   CH.sub.3                                                                           ##STR473##                                                                                   ##STR474##                                                                              NH 103-105                                    963   CH.sub.3                                                                           ##STR475##   OH        NH 170-173                                    964   CH.sub.3                                                                           ##STR476##                                                                                   ##STR477##                                                                              NH 106-109                                    965   CH.sub.3                                                                           ##STR478##   OH        NH 123-125                                    966   CH.sub.3                                                                           ##STR479##                                                                                   ##STR480##                                                                              NH 89-91                                      967   CH.sub.3                                                                           ##STR481##   OH        NH 140-143                                    __________________________________________________________________________

                                      TABLE 57                                     __________________________________________________________________________     Compound                                  m.p. (°C.)                    No.   R.sup.1                                                                           R.sup.2           R           X  or (n.sub.D.sup.20)                  __________________________________________________________________________     968   CH.sub.3                                                                          COOCH.sub.2 CHCH.sub.2                                                                           OH          NH                                      969   CH.sub.3                                                                          COOCH.sub.2 CCH   OH          NH                                      970   CH.sub.3                                                                          CONHCH.sub.3                                                                                      ##STR482## NH                                      971   CH.sub.3                                                                          CONHCH.sub.3      OH          NH                                      972   CH.sub.3                                                                           ##STR483##                                                                                       ##STR484## NH                                      973   CH.sub.3                                                                           ##STR485##       OH          NH                                      974   CH.sub.3                                                                           ##STR486##                                                                                       ##STR487## NH                                      975   CH.sub.3                                                                           ##STR488##       OH          NH                                      976   CH.sub.3                                                                          COSCH.sub.3       OH          NH                                      977   CH.sub.3                                                                          COSC.sub.2 H.sub.5                                                                               OH          NH                                      978   CH.sub.3                                                                          COSC.sub.3 H.sub.7                                                                               OH          NH                                      979   CH.sub.3                                                                          COSC.sub.4 H.sub.9                                                                               OH          NH                                      980   CH.sub.3                                                                           ##STR489##       OH          NH                                      981   CH.sub.3                                                                           ##STR490##       OH          NH 172-176                              982   CH.sub.3                                                                          CH.sub.3                                                                                          ##STR491## NH 115-118                              983   CH.sub.3                                                                          CH.sub.3          OH          NH 168-172                              984   CH.sub.3                                                                          H                 OCH(CH.sub.3)OCOC.sub.4 H.sub.9 -t                                                         NH 52-55                                985   CH.sub.3                                                                          COOH              OH          NH 178-182                              986   CH.sub.3                                                                          COOCH.sub.2 OCH.sub.3                                                                            OCH.sub.2 OCH.sub.3                                                                        NH 145-148                              987   CH.sub.3                                                                           ##STR492##       OH          NH 203-206                              __________________________________________________________________________

                                      TABLE 58                                     __________________________________________________________________________     Compound                         m.p. (°C.)                             No.   R.sup.1                                                                               R.sup.2                                                                               R        X   or (n.sub.D.sup.20)                           __________________________________________________________________________     988   CH.sub.3                                                                              COOC.sub.3 H.sub.7                                                                    OCH.sub.2 CH═CH.sub.2                                                               S                                                 989   CH.sub.3                                                                              COOC.sub.3 H.sub.7                                                                    OH       S                                                 990   CH.sub.3                                                                              COOC.sub.3 H.sub.7 -i                                                                 OH       S                                                 991   CH.sub.3                                                                              COOC.sub.4 H.sub.9                                                                    OH       S                                                 992   CH.sub.3                                                                              CONHC.sub.3 H.sub.7                                                                   OH       S                                                 993   CH.sub.3                                                                              COSC.sub.2 H.sub.5                                                                    OH       S                                                 994   H      COOC.sub.2 H.sub.5                                                                    OH       NH                                                995   Cl     COOC.sub.2 H.sub.5                                                                    OH       NH                                                996   CN     COOC.sub.2 H.sub.5                                                                    OH       NH                                                997   NO.sub.2                                                                              COOC.sub.2 H.sub.5                                                                    OH       NH                                                998   CH.sub.2 Cl                                                                           COOC.sub.2 H.sub.5                                                                    OH       NH                                                999   CH.sub.2 OH                                                                           COOC.sub.2 H.sub.5                                                                    OH       NH                                                1000  CH.sub.2 OCH.sub.3                                                                    COOC.sub.2 H.sub.5                                                                    OH       NH                                                1001  H      COCH.sub.3                                                                            OH       NH                                                1002  H      CHO    OH       NH                                                1003  H      CN     OH       NH                                                1004  H      CH.sub.3                                                                              OH       NH                                                1005  C.sub.2 H.sub.5                                                                       COOC.sub.2 H.sub.5                                                                    OH       NH                                                1006  C.sub.2 H.sub.5                                                                       H      OH       NH                                                __________________________________________________________________________

                                      TABLE 59                                     __________________________________________________________________________      ##STR493##                                                                    Compound                         m.p. (°C.)                             No.   R.sup.1                                                                           R.sup.2     R        X  or (n.sub.D.sup.20)                           __________________________________________________________________________     1007  CH.sub.3                                                                          COOC.sub.3 H.sub.7 -i                                                                      OCH.sub.2 O                                                                             O    120-121.5                                   1008  CH.sub.3                                                                          COOC.sub.3 H.sub.7 -i                                                                      OCH.sub.2 CHCH.sub.2                                                                    O  1.5651                                        1009  CH.sub.3                                                                          COOC.sub.3 H.sub.7 -i                                                                      OH       O  188-191                                       1010  CH.sub.3                                                                          COOCH.sub.3 OCH.sub.2 CHCH.sub.2                                                                    O  118-122                                       1011  CH.sub.3                                                                           ##STR494## OCH.sub.2 CHCH.sub.2                                                                    NH                                               1012  CH.sub.3                                                                           ##STR495## OH       NH                                               1013  CH.sub.3                                                                          H           OH       NH                                               __________________________________________________________________________

Compounds (I) of the present invention can be produced, for example, in accordance with the following processes 1 to 6. ##STR496## (wherein L¹ is a halogen atom, an alkylsulfonyl group, a benzylsulfonyl group or a substituted benzylsulfonyl group, and R, R³, R⁴, A, W, Y, Z and n are as defined above.)

A compound of the formula (I) can be produced by reacting a compound of the formula (II) with a compound of the formula (III) in a suitable solvent in the presence of an at least equal amount of a base at a temperature within a range of from room temperature to the boiling point of the solvent for from 0.5 to 24 hours.

As the base, an alkali metal such as metal sodium or metal potassium, an alkali metal hydride or an alkaline earth metal hydride such as sodium hydride, potassium hydride or calcium hydride, an alkali metal alkoxide such as potassium t-butoxide, an alkali metal carbonate such as sodium carbonate or potassium carbonate, an alkali metal hydrogen carbonate such as sodium hydrogen carbonate or potassium hydrogen carbonate, or an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide, may be used.

As the solvent, a hydrocarbon solvent such as benzene, toluene or xylene, a halogenated hydrocarbon solvent such as dichloromethane or chloroform, an ether solvent such as diethyl ether, tetrahydrofuran or 1,4-dioxane, an ester solvent such as methyl acetate or ethyl acetate, a ketone solvent such as acetone or methyl ethyl ketone, an aprotic polar solvent such as N,N-dimethylformamide, N,N-dimethylacetamide or dimethylsulfoxide, or acetonitrile, may, for example, be used.

The condensed heterocyclic carbonyl derivative (II) as the starting material can be obtained by known methods, for example, the methods disclosed in Bulletin de la Saciete Chimique de France), p. 2763-2766 (1975), J. Indian. Chem. Soc. Vol 45 (5), p. 439-445 (1968), Indian. J. Chem. Section B, 25B (8), p. 870-871 (1986), J. Chem. Soc. Organic Chemistry (1), p. 1-4 (1969), Indian. J. Chem. Section B, 15B (91), p. 1056-1058 (1977), Pract. Heterocyclic. Chem. Academic, p. 55 (1968), Organic Reaction, Vol 20, p. 337 (1973), Helvetica Chemica Acta., Vol 54, p. 959 (1970), J. Org. Chem., Vol 33 (12), p. 4426 (1968), Chemical and Pharmaceutical Bulletin, Vol 25 (11), p. 2988 (1977), and Parmaco, Edizione Scientifica (ITA), Vol 36 (9), p. 794 (1981).

Further, in a case where R in the formula (II) is H, a product wherein R is OH can be obtained by oxidation in accordance with a known method. ##STR497## (wherein R²¹ is an alkyl group, an allyl group, a benzyl group or a trimethylsilylethyl group, and A, W, Y, Z, R³, R⁴ and n are as defined above.)

When R²¹ is an alkyl group, a compound of the formula (V) can be produced by reacting a compound of the formula (IV) in water or in a suitable solvent containing water in the presence of an at least equimolar amount of a base at a temperature within a range of from room temperature to the boiling point of the solvent for from 0.5 to 24 hours, followed by acidifying.

As the base, an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide, an alkali metal carbonate such as sodium carbonate or potassium carbonate, or an alkali metal hydrogen carbonate such as sodium hydrogen carbonate or potassium hydrogen carbonate, may be used.

As the solvent, an alcohol solvent such as methanol, ethanol or 2-propanol, an ether solvent such as diethyl ether, tetrahydrofuran or 1,4-dioxane, a ketone solvent such as acetone or methyl ethyl ketone, an aprotic polar solvent such as N,N-dimethylformamide, N,N-dimethylacetamide or diemthylsulfoxide, or other solvent such as acetonitrile, may, for example, be used.

When R²¹ is an allyl group, a product can be produced by reacting such a compound with dimedone or with an allyl acceptor such as formic acid or n-butylamine in a solvent such as acetonitrile, diemthylformamide or tetrahydrofuran using a palladium catalyst such as tetrakistriphenylphosphine palladium (O) at a temperature within a range of from room temperature to the boiling point of the solvent for from 1 to 24 hours.

Further, when R²¹ is a benzyl group, a product can be produced by hydrogenation in a suitable solvent using a platinum catalyst or palladium catalyst at an ordinary temperature under an ordinary pressure (if required, under heating and under pressure).

When R²¹ is a trimethylsilylethyl group, a product can be produced by reacting such a material with an at least equimolar amount of tetrabutylammonium fluoride or the like in tetrahydrofuran at room temperature.

As the solvent, an alcohol solvent such as methanol or ethanol, an ester solvent such as methyl acetate or ethyl acetate, a ketone solvent such as acetone or methyl ethyl ketone, an ether solvent such as diethyl ether, dioxane or tetrahydrofuran, or acetic acid, may, for example, be used. ##STR498## {wherein Q is a halogen atom, a cyano group, or an imidazolyl group, R²² is an alkoxy group which may be substituted, a benzyloxy group which may be substituted, an isopropylidenaminoxy group, a phenyloxy group which may be substituted, a phenylthio group which may be substituted, an alkenyloxy group, an alkynyloxy group, an alkylthio group, or a group of the formula --NR⁶ R⁷ (wherein each of R⁶ and R⁷ which may be the same or different, is a hydrogen atom, an alkyl group, a phenyl group which may be substituted, an alkylsulfonyl group, or a phenylsulfonyl group which may be substituted, or R⁶ and R⁷ may, together with the nitrogen atom, form a ring), and R³ R⁴ A, W, Y, Z and n are as defined above.}

For the production of a compound of the formula (I) of the present invention, a compound of the formula (V) is reacted with an at least equimolar amount of a condensing agent in a suitable solvent at a temperature within a range of from -10° C. to the boiling point of the solvent for from 0.5 to 24 hours to obtain a compound of the formula (VI). After isolating or without isolating it, it is reacted with a compound of the formula (VII) together with an at least equimolar amount of a base in a suitable solvent at a temperature within a range of from -10° C. to the boiling point of the solvent for from 0.5 to 24 hours, to obtain a compound of the formula (I).

As the condensing agent, thionyl chloride, oxalic acid dichloride, a chlorocarbonic acid ester, carbonyl diimidazole, a cyanophospholic acid ester or a carbodiimide may, for example, be used.

As the base, an alkali metal such as metal sodium or metal potassium, an alkali metal hydride or alkaline earth metal hydride such as sodium hydride, potassium hydride or calcium hydride, an alkali metal alkoxide such as potassium t-butoxide, an alkali metal carbonate such as sodium carbonate or potassium carbonate, or an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide, may, for example, be used.

As the solvent, a hydrocarbon solvent such as benzene, toluene or xylene, a halogenated hydrocarbon solvent such as dichloromethane or chloroform, an ether solvent such as diethyl ether, tetrahydrofuran or 1,4-dioxane, an ester solvent such as methyl acetate or ethyl acetate, a ketone solvent such as acetone or methyl ethyl ketone, an aprotic polar solvent such as N,N-dimethylformamide, N,N-dimethylacetamide or dimethylsulfoxide, or other solvent such as acetonitrile, may, for example, be used. ##STR499## (wherein R³, R⁴, A, W, Y, Z and n are as defined above, and M is an alkali metal, an alkaline earth metal, ammonium or organic ammonium.)

A compound of the formula (VIII) can be produced by reacting the compound of the formula (V) together with an equimolar amount of a base in a suitable solvent at a temperature within a range of from room temperature to the boiling point of the solvent for from 0.5 to 24 hours.

As the base, an alkali metal hydroxide or alkaline earth metal hydroxide such as sodium hydroxide or calcium hydroxide, an alkali metal carbonate or alkaline earth metal carbonate such as sodium carbonate or calcium carbonate, an alkali metal hydride or alkaline earth metal hydride such as sodium hydride, potassium hydride or calcium hydride, an alkali metal alkoxide such as sodium methoxide or sodium ethoxide, an alkali metal hydrogen carbonate such as sodium hydrogen carbonate or potassium hydrogen carbonate, ammonia, or an organic amine such as isopropylamine, may, for example, be used.

As the solvent, a hydrocarbon solvent such as benzene, toluene or xylene, a halogenated hydrocarbon solvent such as dichloromethane or chloroform, an ester solvent such as methyl acetate or ethyl acetate, an alcohol solvent such as methanol, ethanol or 2-propanol, an ether solvent such as diethyl ether, tetrahydrofuran or dioxane, a ketone solvent such as acetone or methyl ethyl ketone, an aprotic polar solvent such as N,N-dimethylformamide, N,N-dimethylacetamide or dimethylsulfoxide, or other solvent such as acetonitrile or water, may, for example, be used. ##STR500## (wherein A, R³, R⁴, W, Y, Z and n are as defined above.)

The compound of the formula (V) of the present invention can be obtained by reacting the compound of the formula (IX) with a suitable oxidizing agent in a suitable solvent at a temperature within a range of from 0° C. to the boiling point of the solvent for from 0.5 to 24 hours.

As the oxidizing agent, a permanganate such as potassium permanganate, a chromic acid such as chromic anhydride, hydrogen peroxide, an organic peracid such as n-chloroperbenzoic acid, or nickel peroxide, may, for example, be used.

As the solvent, a hydrocarbon solvent such as benzene, toluene or xylene, a halogenated hydrocarbon solvent such as dichloromethane or chloroform, an ether solvent such as diethyl ether, tetrahydrofuran or 1,4-dioxane, an ester solvent such as methyl acetate or ethyl acetate, a ketone solvent such as acetone or methyl ethyl ketone, an aprotic polar solvent such as N,N-dimethylformamide, N,N-dimethylacetamide or dimethylsulfoxide, or other solvent such as acetonitrile or water, may, for example, be used. ##STR501## (wherein R²³ is an alkyl group which may be substituted, a benzyl group which may be substituted, an alkenyl group, an alkynyl group, or a 2-trimethylsilylethoxymethyl group, L² is a hydrogen atom, and R³, R⁴, A, W, Y, Z and n are as defined above.)

A compound of the formula (XI) can be produced by reacting a compound of the formula (V) with a compound of the formula (X) in a suitable solvent in the presence of a base at a temperature within a range of from 10° C. to the boiling point of the solvent for from 0.5 to 24 hours.

As the base, an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide, an alkali metal carbonate such as sodium carbonate or potassium carbonate, an alkali metal hydrogen carbonate such as sodium hydrogen carbonate or potassium hydrogen carbonate, or an alkali metal hydride such as sodium hydride, may, for example, be used.

As the solvent, a ketone solvent such as acetone or methyl ethyl ketone, a hydrocarbon solvent such as benzene, toluene or xylene, a halogenated hydrocarbon solvent such as dichloromethane or chloroform, an ether solvent such as diethyl ether, tetrahydrofuran or 1,4-dioxane, an ester solvent such as methyl acetate or ethyl acetate, an aprotic polar solvent such as N,N-dimethylformamide, N,N-dimethylacetamide or dimethylsulfoxide, or other solvent such as acetonitrile, may, for example, be used. ##STR502## (wherein L³ is a leaving group such as a halogen, and R, R¹, R², R³, R⁴, R⁵, W and Z are as defined above, provided that R⁵ excludes a hydrogen atom.)

A compound of the formula (XIV) can be produced by reacting a compound of the formula (XII) with a compound of the formula (XIII) in a suitable solvent in the presence of an at least equimolar amount of a base at a temperature within a range of from -10° C. to the boiling point of the solvent for from 0.5 to 24 hours.

As the base, an alkali metal such as metal sodium or metal potassium, an alkali metal hydride such as sodium hydride or potassium hydride, an alkali metal alkoxide such as potassium t-butoxide, an alkali metal carbonate such as sodium carbonate or potassium carbonate, or an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide, may, for example, be used.

As the solvent, a hydrocarbon solvent such as toluene or xylene, a halogenated hydrocarbon solvent such as dichloromethane or chloroform, an ether solvent such as diethyl ether or tetrahydrofuran, a ketone solvent such as acetone, an aprotic polar solvent such as N,N-dimethylformamide or dimethylsulfoxide, or other solvent such as acetonitrile, may, for example, be used. ##STR503## (wherein R²⁴ is a formyl group or a nitro group, and R³, R⁴, R, W, Y, Z and n are as defined above.)

A compound of the formula (XVI) can be obtained by subjecting the compound of the formula (XV) to a Vilsmeier reaction with phosphorus oxychloride in N,N-dimethylformamide to obtain a formyl product, or reacting it with a nitric acid ester in tetrahydrofuran in the presence of an alcoholate or reacting it with nitronium tetrafluoroborate in acetonitrile or in tetrahydrofuran at a temperature within a range of from -50° C. to the boiling point of the solvent, to obtain a nitro product.

Further, the obtained nitro product may be reduced by a conventional method to obtain an amino product, which can be led to various derivatives.

Among the compounds of the formula (I) of the present invention wherein A is (A-11), a compound of the formula (XIX) can be produced by the following process. ##STR504## (wherein X¹ and X² represent an oxygen atom, a sulfur atom and NR¹⁴ among those defined above, R, R³, R⁴, R¹⁴, Q¹, W, Y, Z and n are as defined above, each of R²⁵ and R²⁶ which may be the same or different, is a chlorine atom, an alkoxy group or a lower alkylthio group.)

A compound of the formula (XIX) can be produced by reacting a compound of the formula (XVII) with a compound of the formula (XVIII) in a suitable solvent in the presence or absence of a base at a temperature within a range of from -30° C. to the boiling point of the solvent, preferably from 0° C. to 120° C., for from 0.5 to 24 hours.

As the base to be used, preferred is an organic base such as triethylamine, pyridine, N,N-diisopropylethylamine or N,N-dimethylaniline. However, an alkali metal hydride or an alkaline earth metal hydride such as sodium hydride, potassium hydride or calcium hydride, an alkali metal alkoxide such as potassium t-butoxide, an alkali metal carbonate such as sodium carbonate or potassium carbonate, or an alkali metal hydrogen carbonate such as sodium hydrogen carbonate or potassium hydrogen carbonate, may also be used.

As the solvent to be used, a hydrocarbon solvent such as benzene, toluene or xylene, a halogenated hydrocarbon solvent such as dichloromethane or chloroform, an ether solvent such as diethyl ether, tetrahydrofuran or 1,4-dioxane, an ester solvent such as ethyl acetate, a ketone solvent such as acetone or methyl ethyl ketone, an aprotic polar solvent such as N,N-dimethylacetamide, N,N-dimethylformamide or dimethylsulfoxide, or other solvent such as acetonitrile, may, for example, be employed.

Among the compounds of the formula (I) of the present invention wherein A is (A-12), a compound of the formula (XII) can be produced by the following process. ##STR505## (wherein R⁵, R¹⁸ and R¹⁹ represent a hydrogen atom and a lower alkyl group among those defined above, X² represents an oxygen atom, a sulfur atom and NR¹⁴ among those defined above, L⁴ is a chlorine atom or a bromine atom, and R, R³, R⁴, R¹⁴, W, Y, Z and n are as defined above.)

A compound of the formula (XXII) can be produced by reacting a compound of the formula (XX) with a compound of the formula (XXI) in a suitable solvent in the presence of a base at a temperature within a range of from 0° C. to the boiling point of the solvent, preferably from 10° C. to 80° C., for from 1 to 20 hours.

As the base to be used, an alkali metal carbonate such as sodium carbonate or potassium carbonate, an alkali metal hydrogen carbonate such as sodium hydrogen carbonate or potassium hydrogen carbonate, an alkali metal hydride or alkaline earth metal hydride such as sodium hydride, potassium hydride or calcium hydride, an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide, an alkali metal alkoxide such as potassium t-butoxide, or an organic base such as triethylamine, pyridine, N,N-diisopropylethylamine or N,N-dimethylaniline, may, for example, be employed.

As the solvent, a hydrocarbon solvent such as benzene, toluene or xylene, a halogenated hydrocarbon solvent such as dichloromethane or chloroform, an ether solvent such as diethyl ether, tetrahydrofuran or 1,4-dioxane, an ester solvent such as ethyl acetate, a ketone solvent such as acetone or methyl ethyl ketone, an aprotic polar solvent such as N,N-dimethylacetamide, N,N-dimethylformamide or dimethylsulfoxide, or other solvent such as acetonitrile, may, for example, be used.

Among the compounds of the formula (I) wherein A is (A-12), a compound of the formula (XXVI) can be produced in accordance with the following process. ##STR506## (wherein R²⁷ is a group of the formula CR¹⁸ R¹⁹ --CH═CHR¹⁸ or a group of the formula CR¹⁸ R¹⁹ C.tbd.CR¹⁸, R¹⁸ and R¹⁹ represent a hydrogen atom and a lower alkyl group among those defined above, X¹ represents an oxygen atom, a sulfur atom and NR¹⁴ among those defined above, and L⁴, R³, R⁴, R¹⁴, W, Y, Z and n are as defined above.)

A compound of the formula (XXV) can be produced by reacting a compound of the formula (XXIII) with a compound of the formula (XXIV) in a suitable solvent in the presence of a base at a temperature within a range of from 0° C. to the boiling point of the solvent, preferably from 20° C. to 80° C., for from 1 to 24 hours.

As the base and the solvent to be used, the same as those described for Process 6 may be employed.

Further, a compound of the formula (XXVI) can be produced by subjecting a compound of the formula (XXV) to an intramolecular cyclization reaction in a suitable solvent in the presence of a suitable catalyst at a temperature of from 0° C. to the boiling point of the solvent, preferably from 20° C. to 150° C., for from 5 to 72 hours.

As the catalyst to be used, an alkali metal carbonate such as potassium carbonate or sodium carbonate, or silver oxide (yellow), may, for example, be mentioned.

As the solvent to be used, preferred is an alcohol solvent such as methanol or ethanol, or an aprotic polar solvent such as N,N-dimethylacetamide, N,N-dimethylformamide or dimethylsulfoxide. However, a hydrocarbon solvent such as benzene, toluene or xylene, a halogenated hydrocarbon solvent such as dichloromethane or chloroform, an ether solvent such as tetrahydrofuran or 1,4-dioxane, an ester solvent such as ethyl acetate, a ketone solvent such as acetone or methyl ethyl ketone, or other solvent such as acetonitrile, may also be used.

Among the compounds of the formula (I) of the present invention wherein A is (A-12), a compound of the formula (XXX) can be produced by the following process. ##STR507## (wherein R¹⁸ and R¹⁹ represent a hydrogen atom and a lower alkyl group among those defined above, X¹ represents an oxygen atom, a sulfur atom and NR¹⁴ among those defined above, and L⁴, R, R³, R⁴, R¹⁴, W, Y, Z and n are as defined above.)

A compound of the formula (XXIX) can be produced by reacting a compound of the formula (XXVII) with a compound of the formula (XXVIII) in a suitable solvent in the presence of a base at a temperature within a range of from 0° C. to the boiling point of the solvent, preferably from 20° C. to 80° C., for from 3 to 24 hours. In this case, the reaction may be accelerated by an addition of an alkali metal iodide such as potassium iodide, as the case requires.

The base and the solvent to be used may be the same as those as described for Process 6.

Further, a compound of the formula (XXX) can be produced by subjecting a compound of the formula (XXIX) to hydrogenation in a suitable solvent in the presence of a palladium carbon catalyst at an ordinary temperature under an ordinary pressure for from 3 to 72 hours.

As the solvent to be used, preferred is an alcohol solvent such as methanol or ethanol. However, a hydrocarbon solvent such as benzene, toluene or xylene, an ether solvent such as tetrahydrofuran or 1,4-dioxane, an ester solvent such as ethyl acetate, a ketone solvent such as acetone or methyl ethyl ketone, or other solvent such as acetonitrile, may also be used.

Among the compounds of the formula (I) of the present invention wherein A is (A-12), a compound of the formula (XXXIV) can be produced by the following process. ##STR508## (wherein R¹⁸ and R¹⁹ represent a hydrogen atom and a lower alkyl group among those defined above, X¹ represents an oxygen atom, a sulfur atom and NR¹⁴ among those defined above, and L⁴, R, R³, R⁴, R¹⁴, W, Y, Z and n are as defined above.)

A compound of the formula (XXXII) can be produced by reacting a compound of the formula (XXVII) with a compound of the formula (XXXI) in a suitable solvent in the presence of a base at a temperature within a range of from 0° C. to the boiling point of the solvent, preferably from 20° C. to 80° C., for from 5 to 24 hours. In this case, the reaction may be accelerated by an addition of an alkali metal iodide such as potassium iodide, as the case requires.

A compound of the formula (XXXIII) can be produced by subjecting a compound of the formula (XXXIV) to an intramolecular cyclization reaction in a suitable solvent in the presence of a base at a temperature within a range of from 0° C. to the boiling point of the solvent, preferably from 20° C. to 80° C., for from 5 to 24 hours.

The base and the solvent to be used may be the same as those described for Process 6.

Further, a compound of the formula (XXXIV) can be produced by reducing a compound of the formula (XXXIII) in a suitable solvent using sodium hydrosulfite at a temperature within a range of from 0° C. to the boiling point of the solvent, preferably from 30° C. to 50° C., for from 0.1 to 1 hour.

As the solvent to be used, preferred is an alcohol solvent such as methanol or ethanol, or water. However, an ether solvent such as tetrahydrofuran or 1,4-dioxane, a ketone solvent such as acetone or methyl ethyl ketone, or other solvent such as acetonitrile, may be used in combination, as the case requires.

Now, the processes for the production of the compounds of the present invention, as well as methods for preparation of formulations and methods for application will be specifically described with reference to Examples.

BEST MODE FOR CARRYING OUT THE INVENTION EXAMPLE 1 Preparation of 5-(4,6-dimethoxypyrimidin-2-yl)oxy-4-formyl-3-methylbenzothiophene (Compound No. 104)

A mixture comprising 2.1 g of 4-formyl-5-hydroxy-3-methylbenzothiophene, 2.4 g of 4,6-dimethoxy-2-methylsulfonylpyrimidine and 1.8 g of potassium carbonate in 30 ml of N,N-dimethylformamide, was heated and stirred at 70° C. for 3 hours. The mixture was returned to room temperature, then poured into water and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous sodium sulfate. Then, it was concentrated under reduced pressure, and the oily substance thereby obtained was purified by silica gel column chromatography (n-hexane/ethyl acetate=10/1) to obtain 3.1 g (yield: 86%) of the desired compound.

EXAMPLE 2 Preparation of 5-(4,6-dimethoxypyrimidin-2-yl)oxy-3-methylbenzothiophene -4-carboxylic acid (Compound No. 105)

0.6 g of 5-(4,6-dimethoxypyrimidin-2-yl)oxy-4-formyl-3-methylbenzothiophene was dissolved in 80 ml of acetone. While stirring the solution at room temperature, 0.6 g of potassium permanganate dissolved in 10 ml of water was dropwise added thereto over a period of 15 minutes, and the mixture was further stirred at room temperature for 4 hours. It was then concentrated under reduced pressure to remove acetone, and then a saturated sodium bicarbonate aqueous solution was added thereto to make the mixture alkaline. The mixture was extracted with ethyl acetate, and then the aqueous layer was precipitated with 10% hydrochloric acid. The precipitated crystals were collected by filtration and washed with water to obtain 0.47 g (yield: 76%) of the desired compound.

EXAMPLE 3 Preparation of Benzyl 5-(4,6-Dimethoxypyrimidin-2-yl)-oxy-3-ethoxycarbonyl-2-methylbenzofuran-4-carboxylate (Compound No. 1)

A mixture comprising 12.88 g of benzyl 3-ethoxycarbonyl-5-hydroxy-2-methylbenzofuran-5carboxylate, 8.33 g of 4,6-dimethoxy-2-methylsulfonylpyrimidine and 5.53 g of potassium carbonate in 150 ml of N,N-dimethylformamide, was heated and stirred at 70° C. for 3 hours. The mixture was returned to room temperature, then poured into ice water and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous sodium sulfate. It was concentrated under reduced pressure, and the oily substance thereby obtained was purified by silica gel column chromatography (n-hexane/ethyl acetate=4/1) to obtain 14.45 g (yield: 81%) of the desired compound.

EXAMPLE 4 Preparation of 5-(4,6-Dimethoxypyrimidin-2yl)oxy-3-ethoxycarbonyl-2-methylbenzofuran-4-carboxylic Acid (Compound No. 2)

A mixture comprising 14.4 g of benzyl 5-(4,6-dimethoxypyrimidin-2-yl)oxy-3-ethoxycarbonyl-2-methylbenzofuran-4-carboxylate and 4.52 g of 10% palladium carbon in 100 ml of ethanol, was subjected to hydrogenation under an ordinary pressure while stirring at room temperature. After completion of the reaction, an insoluble matter was separated by filtration, and the filtrate was concentrated under reduced pressure, whereupon the precipitated crystals were washed with a solvent mixture of diethyl ether/n-hexane to obtain 10.47 g (yield: 89%) of the desired compound.

EXAMPLE 5 Preparation of Pivaloyloxymethyl 5-(4,6-Dimethoxypyrimidin-2-yl)oxy-3-ethoxycarbonyl-2-methylbenzofuran-4-carboxylate (Compound No. 4)

A mixture comprising 0.40 g of 5-(4,6-dimethoxypyrimidin-2-yl)oxy-3-ethoxycarbonyl-2-methylbenzofuran-4-carboxylic acid, 0.26 g of chloromethyl pivalate and 0.21 g of potassium carbonate in 20 ml of N,N-dimethylformamide, was stirred at room temperature for 6 hours, then poured into ice water and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous sodium sulfate. It was concentrated under reduced pressure, and the oily substance thereby obtained was purified by silica gel column chromatography (n-hexane/ethyl acetate=4/1) to obtain 0.43 g (yield: 84%) of the desired compound.

EXAMPLE 6 Preparation of Methyl 5-(4,6-Dimethoxypyrimidin-2-yl)oxybenzoxazol-4-carboxylate (Compound No. 446)

A mixture comprising 0.6 g of methyl 5-hydroxybenzoxazol-4-carboxylate, 0.6 g of 2-chloro-4,6-dimethoxypyrimidine and 0.7 g of potassium carbonate in 30 ml of N,N-dimethylformamide, was heated and stirred at 115° C. for two hours. The mixture was returned to room temperature, then poured into water and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The oily substance thereby obtained was purified by silica gel column chromatography (n-hexane/ethyl acetate=5/1) to obtain 0.4 g (yield: 39%) of the desired compound.

EXAMPLE 7 Preparation of Methyl 6-(4,6-Dimethoxy-1,3,5-triazin-2-yl)oxybenzoxazol-7-carboxalate (Compound No. 464)

0.6 g of methyl 6-hydroxyybenzoxazol-7-carboxylate, 0.55 g of 2-chloro-4,6-dimethoxy-1,3,5-triazine and 0.5 g of potassium carbonate in 30 ml of N,N-dimethylformamide were heated and stirred at 115° C. for 3 hours. The mixture was returned to room temperature, then poured into water and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The oily substance thereby obtained was purified by silica gel column chromatography (n-hexane/ethyl acetate=5/1) to obtain 0.6 g (yield: 58%) of the desired compound.

EXAMPLE 8 Preparation of Methyl 5-(4,6-Dimethoxypyrimidin-2-yl)oxy-2-ethoxy-2,3-dihydrobenzofuran-4-carboxylate (Compound No. 507)

A mixture comprising 1.0 g of methyl 2-ethoxy-5-hydroxy-2,3-dihydrobenzofuran-4-carboxylate, 1.0 g of 4,6-dimethoxy-2-methylsulfonylpyrimidine and 0.78 g of potassium carbonate in 30 ml of N,N-dimethylformamide, was heated and stirred at 100° C. for two hours. The mixture was returned to room temperature, then poured into water and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous sodium sulfate. It was concentrated under reduced pressure, and the oily substance thereby obtained was purified by silica gel column chromatography (n-hexane/ethyl acetate=4/1) to obtain 1.5 g (yield: 95%) of the desired compound.

EXAMPLE 9 Preparation of 5-(4,6-Dimethoxypyrimidin-2-yl)oxy-2-ethoxy-2,3-dihydrobenzofuran-4-carboxylic Acid (Compound No. 508)

While stirring 1.2 g of methyl 5-(4,6-dimethoxypyrimidin-2-yl)oxy-2-ethoxy-2,3-dihydrobenzofuran-4-carboxylate in 20 ml of dimethylsulfoxide at room temperature, 2 ml of a 2N sodium hydroxide aqueous solution was dropwise added thereto over a period of 10 minutes and then the mixture was further stirred for 15 hours. The mixture was poured into water and extracted with diethyl ether. Then, the aqueous layer was acidified with 10% hydrochloric acid, and precipitated crystals were extracted with ethyl acetate, and the organic layer was washed with water and then dried over anhydrous sodium sulfate. It was concentrated under reduced pressure, and the oily substance thereby obtained was purified by silica gel column chromatography (n-hexane/ethyl acetate=1/1) to obtain 1.0 g (yield: 87%) of the desired compound.

EXAMPLE 10 Preparation of Sodium 3-Benzoyl-5-(4,6-dimethoxypyrimidin-2-yl)oxy-2-trifluoromethylbenzofuran-4-carboxylate (Compound No. 77)

While stirring 0.35 g of sodium hydride in 30 ml of N,N-dimethylformamide at room temperature, 1.73 g of 3-benzoyl-5-hydroxy-2-trifluoromethylbenzofuran-4-carboxylic acid was gradually added thereto. After completion of the addition, the mixture was further stirred for one hour. While stirring this mixture at room temperature, 1.08 g of 4,6-dimethoxy-2-methylsulfonylpyrimidine was added thereto, and then the mixture was stirred at 70° C. for 3 hours. The mixture was returned to room temperature and poured into water. Precipitated crystals were separated by filtration and washed with water and acetone to obtain 1.02 g (yield: 40.5%) of the desired compound.

EXAMPLE 11 Preparation of Benzyl 5-(4,6-Dimethoxy-1,3,5-triazin-2-yl)oxy-2-methyl-3-methoxycarbonylbenzofuran-4-carboxylate (Compound No. 32).

A mixture comprising 2 g of benzyl 5-hydroxy-2-methyl-3-methoxycarbonylbenzofuran-4-carboxylate, 1 g of 4,6-dimethoxy-2-methylsulfonyl-1,3,5-triazine and 1 g of potassium carbonate in 20 ml of N,N-dimethylformamide, was heated and stirred at 70° C. for two hours. The mixture was returned to room temperature, poured into ice water and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous sodium sulfate. Then, it was concentrated under reduced pressure, and the obtained solid was thoroughly washed with ethanol to obtain 2.4 g (yield: 86%) of the desired compound.

EXAMPLE 12 Preparation of Methyl 6-(4,6-Dimethoxypyrimidin-2-yl)oxy-3-methyl-benzisoxazol-7-carboxylate (Compound No. 487)

A mixture comprising 1.3 g of methyl 6-hydroxy-3-methyl-benzisoxazol-7-carboxylate, 1.4 g of 4,6-dimethoxy-2-methylsulfonylpyrimidine and 1 g of potassium carbonate in 20 ml of N,N-dimethylformamide, was heated and stirred at 70° C. for two hours. The mixture was returned to room temperature, poured into ice water and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous sodium sulfate. Then, it was concentrated under reduced pressure, and the obtained crystals were thoroughly washed with isopropyl ether to obtain 1.6 g (yield: 73%) of the desired compound.

EXAMPLE 13 Preparation of 6-(4,6-Dimethoxypyrimidin-2-yl)oxy-3-methyl-benzisoxazol-7-carboxylic Acid (Compound No. 488).

While heating and stirring 1.0 g of methyl 6-(4,6-dimethoxypyrimidin-2-yl)oxy-3-methylbenzisoxazol-7-carboxylate in 20 ml of N,N-dimethylsulfoxide at 70° C., 1.7 ml of a 2N sodium hydroxide aqueous solution was dropwise added thereto over a period of 10 minutes. Then, the mixture was further heated and stirred at 70° C. for 30 minutes. The mixture was returned to room temperature, then poured into water and extracted with diethyl ether. The aqueous layer was acidified with 10% hydrochloric acid, and precipitated crystals were extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous sodium sulfate. It was then concentrated under reduced pressure, and the crystals thereby obtained were washed with isopropyl ether to obtain 0.7 g (yield: 71%) of the desired compound.

EXAMPLE 14 Preparation of Sodium 6-(4,6-Dimethoxypyrimidin-2-yl)oxy-3-methoxycarbonyl-2-methylbenzofuran-4-carboxylate (Compound No. 130)

While stirring 0.5 g of 5-(4,6-dimethoxypyrimidin-2-yl)oxy-3-methoxycarbonyl-2-methyl-benzofuran-4-carboxylic acid in 5 ml of tetrahydrofuran at room temperature, 0.05 g of 60% sodium hydride was added thereto. The mixture was stirred at room temperature for 6 hours. Then, precipitated crystals were collected by filtration and washed with isopropyl ether to obtain 0.40 g (yield: 75%) of the desired compound.

EXAMPLE 15 Preparation of N-[5-(4,6-dimethoxypyrimidin-2-yl)oxy-3-ethoxycarbonyl-2-methylbenzofuran-4-carbonyl]imidazole (Compound No. 16)

While stirring 0.8 g of 5-(4,6-dimethoxypyrimidin-2-yl)oxy-3-ethoxycarbonyl-2-methyl-benzofuran-4-carboxylic acid in 30 ml of tetrahydrofuran at room temperature, 0.36 g of carbonyldiimidazole was added thereto. The mixture was stirred at room temperature for one hour and then concentrated under reduced pressure. The residue was dissolved in ethyl acetate and washed with water. It was dried over anhydrous sodium sulfate and then concentrated under reduced pressure, and the crystals thereby obtained were washed with n-hexane to obtain 0.81 g (yield: 90%) of the desired compound.

EXAMPLE 16 Preparation of 4-Allyloxycarbonyl-5-(4,6-dimethoxypyrimidin-2-yl)oxy-2-methylbenzofuran-3-carboxylic Acid (Compound No. 371)

A mixture comprising 54.2 g of 4-allyloxycarbonyl-5-hydroxy-2-methylbenzofuran-3-carboxylic acid, 47 g of 4,6-dimethoxy-2-methylsulfonylpyridine and 65 g of potassium carbonate in 200 ml of N,N-dimethylformamide, was heated and stirred at 70° C. for two hours. The mixture was returned to room temperature, and then the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous magnesium sulfate. Crystals obtained by concentration under reduced pressure, were washed with isopropyl ether to obtain 79.2 g (yield: 98%) of the desired compound.

EXAMPLE 17 Preparation of 4-Allyloxycarbonyl-5-(4,6-dimethoxypyrimidin-2-yl)oxy-2-methylbenzofuran-2-carbonyl Chloride (Compound No. 254)

30.4 g of 4-allyloxycarbonyl-5-(4,6-dimethoxypyrimidin-2-yl)oxy-2-methylbenzofuran-3-carboxylic acid was dissolved in 73 ml of thionyl chloride, and the solution was heated and stirred at 60° C. for 30 minutes. It was returned to room temperature, and then thionyl chloride was concentrated under reduced pressure. Toluene was added thereto, followed by further concentration. To the obtained oily substance, hexane was added for crystallization to obtain 31.4 g (yield: 99%) of the desired compound.

EXAMPLE 18 Preparation of Allyl 5-(4,6-Dimethoxypyrimidin-2-yl)oxy-3-dimethylcarbamoyl-2-methylbenzofuran-4-carboxylate (Compound No. 248)

3.0 g of 4-allyloxycarbonyl-5-(4,6-dimethoxypyrimidin-2-yl)oxy-2-methylbenzofuran-3-carbonyl chloride was dissolved in 13 ml of dichloromethane, and 1.5 g of a 50% dimethylamine aqueous solution was dropwise added thereto under cooling with ice. After stirring for 30 minutes, the reaction solution was poured into water and extracted with dichloromethane. The organic layer was washed with water and then dried over anhydrous sodium sulfate. The oily substance obtained by concentration under reduced pressure, was purified by silica gel column chromatography (n-hexane/ethyl acetate=4/1) to obtain 1.84 g (yield: 60%) of the desired compound.

EXAMPLE 19 Preparation of 5-(4,6-Dimethoxypyrimidin-2-yl)oxy-3-dimethylcarbamoyl-2-methylbenzofuran-4-carboxylic Acid (Compound No. 247)

1.40 g of allyl 5-(4,6-dimethoxypyrimidin-2-yl)oxy-3-dimethylcarbamoyl-2-methylbenzofuran-4-carboxylate and 0.29 g of formic acid were dissolved in 12 ml of tetrahydrofuran, and 37 mg of tetrakistriphenylphosphine palladium (0) was added thereto under a nitrogen atmosphere. The mixture was heated and stirred at 50° C. for 3 hours. The mixture was returned to room temperature, and then isopropyl ether was added to the reaction solution. Precipitated crystals were collected by filtration to obtain 1.02 g (yield: 80%) of the desired compound.

EXAMPLE 20 Preparation of Allyl 5-(4,6-Dimethoxypyrimidin-2-yl)oxy-3-ethylthiocarbonyl-2-methylbenzofuran-4-carboxylate (Compound No. 152)

3.0 g of 4-allyloxycarobnyl-5-(4,6-dimethoxypyrimidin-2-yl)oxy-2-methylbenzofuran-3-carbonyl chloride and 0.88 g of triethylamine were dissolved in 13 ml of dichloromethane, and 0.56 g of ethyl mercaptan was dropwise added thereto under cooling with ice. After stirring for 30 minutes, the reaction solution was poured into water and extracted with dichloromethane. The organic layer was washed with water, then dried over anhydrous sodium sulfate and concentrated under reduced pressure. The oily substance thereby obtained was purified by silica gel column chromatography (n-hexane/ethyl acetate=4/1) to obtain 1.74 g (yield: 55%) of the desired compound.

EXAMPLE 21 Preparation of 5-(4,6-Dimethoxypyrimidin-2-yl)oxy-3-ethylthiocarbonyl-2-methylbenzofuran-4-carboxylic Acid (Compound No. 153)

1.60 g of allyl 5-(4,6-dimethoxypyrimidin-2-yl)oxy-3-ethylthiocarbonyl-2-methylbenzofuran-4-carboxylate and 0.54 g of dimedone were dissolved in 14 ml of tetrahydrofuran, and 40 mg of tetrakistriphenylphosphine palladium (0) was added thereto under a nitrogen atmosphere. The mixture was stirred at room temperature for 3 hours. The reaction solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=2/1) to obtain 1.33 g (yield: 91%) of the desired compound.

EXAMPLE 22 Preparation of 2-Trimethylsilylethoxymethyl 5-(4,6-Dimethoxypyrimidin-2,yl)oxy-3-(4-methoxybenzyloxycarbonyl)-2-methylbenzofuran-4-carboxylate (Compound No. 369)

13.5 g of 5-(4,6-dimethoxypyrimidin-2-yl)oxy-3-(4-methoxybenzyloxycarbonyl)-2-methylbenzofuran-4-carboxylic acid and 3.3 g of triethylamine were dissolved in 120 ml of dichloromethane, and 5.0 g of 2-trimethylsilylethoxymethyl chloride was dropwise added thereto under cooling with ice. After stirring for 30 minutes, the reaction solution was poured into water and extracted with dichloromethane. The organic layer was washed with water, then dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue thereby obtained was purified by silica gel column chromatography (n-hexane/ethyl acetate=4/1) to obtain 14.0 g (yield: 82%) of the desired compound.

EXAMPLE 23 Preparation of Methyl 6-[(4,6-Dimethoxypyrimidin-2-yl)oxy]quinolin-5-carboxylate (Compound No. 904)

0.8 g of methyl 6-hydroxyquinolin-5-carboxylate, 0.96 g of 4,6-dimethoxy-2-methylsulfonylpyridine and 0.82 g of potassium carbonate were stirred in 30 ml of N,N-dimethylformamide at 80° C. for 3 hours. The mixture was returned to room temperature, then poured into ice water and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous magnesium sulfate. The residue obtained by concentration under reduced pressure, was crystallized from a solvent mixture of dichloromethane/isopropyl ether to obtain 1.21 g (yield: 89.0%) of the desired compound. mp: 160°-162° C.

EXAMPLE 24 Preparation of 6-[(4,6-Dimethoxypyrimidin-2-yl)oxy]quinolin-5-carboxylic Acid (Compound No. 903)

0.8 g of methyl 6-[(4,6-dimethoxypyrimidin-2-yl)oxy]quinolin-5-carboxylate was dissolved in 10 ml of methanol and 20 ml of methoxyethane, and 5 ml of an aqueous solution containing 0.39 g of potassium hydroxide was added thereto at 40° C. The mixture was extracted with dichloromethane. The aqueous layer was acidified (pH=4) with a 10% hydrochloric acid aqueous solution, and formed precipitates were collected by filtration and dried to obtain 0.5 g (yield: 66.0%) of the desired compound. mp: 195°-198° C.

EXAMPLE 25 Preparation of Benzyl 5-[(4,6-Dimethoxypyrimidin-2-yl)oxy]2-methylindol-4-carboxylate (Compound No. 664)

A mixture comprising 2.2 g of benzyl 5-hydroxy-2-methylindol-4-carboxylate, 1.7 g of 4,6-dimethoxy-2-methylsulfonylpyrimidine and 1.3 g of potassium carbonate in 20 ml of N,N-dimethylformamide, was heated and stirred at a temperature of from 70° to 80° C. for two hours. The mixture was returned to room temperature, then poured into ice water and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous magnesium sulfate. The residue obtained by concentration under reduced pressure, was crystallized from isopropyl ether to obtain 2.8 g (yield: 85%) of the desired product. mp: 135°-139° C.

EXAMPLE 26 Preparation of Benzyl 5-[(4,6-Dimethoxypyrimidin-2-yl)oxy]-3-formyl-2-methylindol-4-carboxylate (Compound No. 680)

0.46 ml of phosphorus oxychloride was dropwise added to 1.8 ml of N,N-dimethylformamide under cooling with ice, and the mixture was stirred for 30 minutes. Then, 2.3 g of benzyl 5-[(4,6-dimethoxypyrimidin-2-yl)oxy]-2-methylindol-4-carboxylate was dissolved in 10 ml of N,N-dimethylformamide, and the solution was dropwise added to the above mixture under cooling with ice. The mixture was stirred for 30 minutes, and then poured into ice water. An aqueous sodium hydroxide solution was added thereto for adjustment to pH9, followed by extraction with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate. The residue obtained by concentration under reduced pressure, was crystallized from isopropyl ether to obtain 2 g (yield: 81.5%) of the desired compound. mp: 148°-149° C.

EXAMPLE 27 Preparation of Allyl 5-[(4,6-Dimethoxypyrimidin-2-yl)oxy]-2-methyl-3-nitroindol-4-carboxylate (Compound No. 759)

2.0 g of allyl 5-[(4,6-dimethoxypyrimidin-2-yl)oxy]-2-methylindol-4-carboxylate was dissolved in 25 ml of acetonitrile, and the solution was cooled to -30° C. 16.3 ml of a 0.5M sulfolane solution of nitronium tetrafluoroborate was dropwise added thereto, and the mixture was stirred for 5 hours. After adding 2 ml of aqueous ammonia, the mixture was returned to room temperature and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous sodium sulfate. Crystals obtained by concentration under reduced pressure, were washed with hexane to obtain 1.23 g (yield: 55%) of the desired compound.

EXAMPLE 28 Preparation of Allyl 3-Amino-5-[(4,6-dimethoxypyrimidin-2-yl)oxy]-2-methylindol-4-carboxylate (Compound No. 722)

3.4 g of allyl 5-[(4,6-dimethoxypyrimidin-2-yl)oxy]-2-methyl-3-nitroindol-4-carboxylate was dissolved in 50 ml of methanol, and 5 ml of concentrated hydrochloric acid was added thereto. Then, 4.9 g of tin powder was gradually added at room temperature. Them, the mixture was stirred at room temperature for 12 hours. The solid was filtered off, and then residue was concentrated under reduced pressure and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous sodium sulfate. The residue obtained by concentration under reduced pressure, was crystallized from isopropyl ether to obtain 2.5 g (yield: 79%) of the desired product. mp: 132°-135° C.

EXAMPLE 29 Preparation of Allyl 3-Acetylamino-5-[(4,6-dimethoxypyrimidin-2-yl)oxy]-2-methylindol-4-carboxylate (Compound No. 735)

0.5 g of allyl 5-[(4,6-dimethoxypyrimidin-2-yl)oxy]-2-methylindol-4-carboxylate was dissolved in 10 ml of pyridine, and 0.16 g of acetic anhydride was added thereto. The mixture was stirred for 12 hours. The reaction solution was poured into ice water and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous magnesium sulfate. The residue obtained by concentration under reduced pressure, was crystallized with isopropyl ether to obtain 0.49 g (yield: 87%) of the desired compound. mp: 177°-180° C.

EXAMPLE 30 Preparation of 3-Acetylamino-5-[(4,6-dimethoxypyrimidin-2yl)oxy]-2-methylindol-4-carboxylic Acid (Compound No. 736)

0.49 g of allyl 3-acetylamino-5-[(4,6-dimethoxypyrimidin-2-yl)oxy]-2-methylindol-4-carboxylate was dissolved in 10 ml of tetrahydrofuran, and 0.1 g of dimedone and 0.01 g of tetrakistriphenylphosphine palladium were added thereto. The mixture was stirred at room temperature for 4 hours. Crystals obtained by concentration under reduced pressure, was washed with isopropyl ether to obtain 0.41 g (yield: 93%) of the desired compound. mp: 230°-233° C.

EXAMPLE 31 Preparation of Benzyl-1-benzoyl-5-[(4,6-dimethoxypyrimidin-2-yl)oxy]-3-ethoxycarbonyl-2-methylindol-4-carboxylate (Compound No. 796)

1.5 g of benzyl 5-[(4,6-dimethoxypyrimidin-2-yl)oxy]-3-ethoxycarbonyl-2-methylindol-4-carboxylate was dissolved in 50 ml of tetrahydrofuran, and 0.176 g of 60% sodium hydride was added thereto. The mixture was stirred at room temperature for 30 minutes. Then, 0.51 g of benzoyl chloride was dropwise added thereto at room temperature, and the mixture was stirred for 4 hours. After concentration under reduced pressure, the mixture was poured into ice water and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous magnesium sulfate. The residue obtained by concentration under reduced pressure, was crystallized from isopropyl ether to obtain 1.67 g (yield: 92%) of the desired compound. mp: 128°-132.5° C.

EXAMPLE 32 Preparation of 1-Benzoyl-5-[(4,6-dimethoxypyrimidin-2-yl)oxy]-3-ethoxycarbonyl-2-methylindol-4-carboxylic Acid (Compound No. 797)

1.6 g of benzyl 1-benzoyl-5-[(4,6-dimethoxypyrimidin-2-yl)oxy]-3-ethoxycarbonyl-2-methylindol-4-carboxylate was dissolved in 50 ml of ethyl acetate, and 0.1 g of 10% palladium carbon was added thereto. Then, catalytic reduction was conducted. Insoluble matters were filtered off, and then filtrate was concentrated under reduced pressure. The residue thereby obtained was washed with isopropyl ether to obtain 1.28 g (yield: 97%) of the desired compound. mp: 113°-115° C.

EXAMPLE 33 Preparation of (2-Trimethylsilyl)ethyl 6-[(4,6-Dimethoxypyrimidin-2-yl)oxy]-2-oxobenzoxazolin-7-carboxylate (Compound No. 853)

1.18 g of triphosgene was gradually added at room temperature to a mixture comprising 2.45 g of (2-trimethylsilyl)ethyl 3-amino-2-hydroxy-6-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoate and 5 ml of triethylamine in 20 ml of dichloromethane. The mixture was stirred at room temperature for one hour, then poured into water and extracted with ethyl acetate. The organic layer was washed with water, 10% hydrochloric acid and a saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate. The residue obtained by concentration under reduced pressure, was purified by silica gel column chromatography to obtain 2.25 g (yield: 97%) of the desired compound. (Yield: 86.5%) Refractive index: unmeasurable

EXAMPLE 34 Preparation of (2-Trimethylsilyl)ethyl 7-[(4,6-Dimethoxypyrimidin-2-yl)oxy]-3-oxo-3,4-dihydro-2H-1,4-benzooxadin-8-carboxylate (Compound No. 878)

0.60 g of chloroacetyl chloride was gradually dropwise added at 10° C. to a mixture comprising 2.04 g of (2-trimethylsilyl)ethyl 3-amino-2-hydroxy-6-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoate and 1.38 g of potassium carbonate in 15 ml of N,N-dimethylformamide, and then the mixture was gradually returned to room temperature and stirred for 5 hours. Further, the mixture was stirred at 50° C. for two hours to complete the reaction. The mixture was returned to room temperature, then poured into water, adjusted to pH3 with 10% hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The residue obtained by concentration under reduced pressure, was purified by silica gel column chromatography to obtain 1.01 g (yield: 41.8%) of the desired compound. mp: 148°-150° C.

EXAMPLE 35 Preparation of (2-Trimethylsilyl)ethyl 7-[(4,6-Dimethoxypyrimidin-2-yl)oxy]-2-methylene-3,4-dihydro-2H-1,4-benzoxadin-8-carboxylate (Compound No. 896)

A mixture comprising 4.20 g of (2-trimethylsilyl)ethyl 3-amino-2-hydroxy-6-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoate, 1.68 g of sodium carbonate and 1.42 g of propargyl bromide in 20 ml of N,N-dimethylformamide was heated and stirred at 50° C. for 4 hours. The mixture was returned to room temperature, then poured into water and extracted with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The residue obtained by concentration under reduced pressure, was purified by silica gel column chromatography to obtain 2.90 g (yield: 63.9%) of (2-trimethylsilyl)ethyl 2-hydroxy-3-propargylamino-6-[(4,6-dimethoxypryrimidin-2-yl)oxy]benzoate.

A mixture comprising 2.80 g of (2-trimethylsilyl)ethyl 2-hydroxy-3-propargylamino-6-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoate thus obtained and 0.20 g of mercury oxide (yellow) in 10 ml of N,N-dimethylfromamide was heated and stirred under a nitrogen stream at 150° C. for two hours. The mixture was returned to room temperature, then poured into water and extracted with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The residue obtained by concentration under reduced pressure, was purified by silica gel column chromatography to obtain 1.80 g of the desired compound. Refractive index: unmeasurable

EXAMPLE 36 Preparation of (2-Trimethylsilyl)ethyl 7-[(4,6-Dimethoxypyrimidin-2-yl)oxy]-3-methyl-3,4-dihydro-2H-1,4-benzooxadin-8-carboxylate (Compound No. 890)

1.20 g of chloroacetone was gradually dropwise added at 10° C. to a mixture comprising 3.50 g of (2-trimethylsilyl)ethyl 2-hydroxy-3-nitro-6-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoate, 1.80 g of potassium carbonate and 1.33 g of potassium iodide in 20 ml of acetone. Then, mixture was gradually returned to room temperature and stirred for 8 hours. Insoluble matters were filtered off, and the filtrate was concentrated under reduced pressure, poured into water and extracted with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The residue obtained by concentration under reduced pressure, was purified by silica gel column chromatography to obtain 3.70 g (yield: 63.9%) of (2-trimethylsilyl)ethyl 2-acetonyloxy-3-nitro-6-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoate (yield: 93.7%)

3.60 g of (2-trimethylsilyl)ethyl-2-acetonitrileoxy-3-nitro-6-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoate thus obtained was subjected to catalytic reduction under an ordinary pressure in 100 ml of methanol by means of 0.5 g of 10% palladium carbon. The reaction was terminated when the theoretical amount of about 700 ml of hydrogen was consumed. Palladium carbon was filtered off, and the filtrate was concentrated under reduced pressure. The residue thereby obtained was purified by silica gel column chromatography to obtain 3.10 g (yield: 94.8%) of the desired compound. Refractive index: unmeasurable

EXAMPLE 37 Preparation of (2-Trimethylsilyl)ethyl 7-[(4,6-Dimethoxypyrimidin-2-yl)oxy]-3,4-dihydro-2H-1,4-benzooxadin-8-carboxylate (Compound No. 884)

A mixture comprising 3.50 g of (2-trimethylsilyl)ethyl 2-hydroxy-3-nitro-6-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoate, 3.40 g of potassium carbonate and 9.40 g of 1,2-dibromoethane in 20 ml of N,N-dimethylformamide was heated and stirred at 80° C. for two hours. The mixture was returned to room temperature, then poured into water and extracted with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The residue obtained by concentration under reduced pressure, was purified by silica gel column chromatography to obtain 3.60 g (yield: 82.8%) of (2-trimethylsilyl)ethyl 2-(2-bromoethoxy)-3-nitro-6-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoate.

3.60 g of (2-trimethylsilyl)ethyl 2-(2-bromoethoxy-3-nitro-6-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoate thus obtained and 7.00 g of 70% sodium hydrosulfite in a solvent mixture of water (15 ml) and methanol (30 ml) were stirred at room temperature for 20 minutes. The mixture was poured into water, saturated with sodium chloride and extracted with ethyl acetate. The organic layer was concentrated under reduced pressure and then extracted with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. 3.10 g of (2-trimethylsilyl)ethyl 3-amino-2-(2-bromoethoxy)-6-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoate was obtained by concentration under reduced pressure. This product was used for the next reaction without purification. (Yield: 91.2%)

3.10 g of (2-trimethylsilyl)ethyl 3-amino-2-(2-bromoethoxy)-6-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoate and 2.76 g of potassium carbonate in 10 ml of N,N-dimethylformamide were stirred at a temperature of from 60° C. to 80° C. for 3 hours. The mixture was returned to room temperature, then poured into water and extracted with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. 1.95 g (yield: 75.0%) of the desired compound was obtained by concentration under reduced pressure. Refractive index: 1.5333

EXAMPLE 38 Preparation of 7-[(4,6-Dimethoxypyrimidin-2-yl)oxy]-3,4-dihydro-2H-1,4-benzoxadin-8-carboxylic Acid (Compound No. 885)

15 ml of 1M tetrahydrofuran solution of tetrabutylammonium fluoride trihydrate was added to 1.65 g of (2-trimethylsilyl)ethyl 7-[(4,6-dimethoxypyrimidin-2-yl)oxy]-3,4-dihydro-2H-1,4-benzoxadin-8-carboxylate obtained in Example 39 in 30 ml of tetrahydrofuran, and the mixture was stirred at room temperature for 3 hours. The mixture was concentrated under reduced pressure, poured into water, adjusted to pH5 with a 20% citric acid aqueous solution and extracted with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The residue obtained by concentration under reduced pressure, was crystallized from isopropyl ether to obtain 0.87 g (yield: 68.5%) of the desired compound. mp: 160°-164° C.

The herbicide of the present invention comprises a condensed heterocyclic derivative of the formula (I) as an active ingredient.

For the compound of the present invention to be used as a herbicide, the compound of the present invention may be used by itself. However, it may be used in the form of a formulation such as a dust, a wettable powder, an emulsifiable concentrate, a microgranule or a granule by blending it with a carrier which is commonly used for formulations, a surfactant, a dispersant or an adjuvant.

The carrier to be used for such formulations, may, for example, be a solid carrier such as Jeaklite, talc, bentonite, clay, kaolin, diatomaceous earth, fine silica, vermiculite, calcium carbonate, slaked lime, silica sand, ammonium sulfate or urea, or a liquid carrier such as isopropyl alcohol, xylene, cyclohexane or methylnaphthalene.

As the surfactant and dispersant, a metal salt of alkylbenzenesulfonic acid, a metal salt of dinaphthylmethane disulfonic acid, a salt of alcohol sulfuric acid ester, an alkylaryl sulfonate, a lignin sulfonate, a polyoxyethylene glycol ether, a polyoxyethylene alkylaryl ether or a polyoxyethylene sorbitol monoalkylate may, for example, be mentioned.

The adjuvant may, for example, be carboxymethyl cellulose, polyethylene glycol or gum arabic.

In practical use, the herbicide may be diluted to a suitable concentration before application, or may be directly applied.

The herbicide of the present invention may be used for application to foliage, soil or water surface. The blending proportion of the active ingredient is suitably selected as the case requires. However, in a case of a dust or a granule, the proportion of the active ingredient is selected suitably within a range of from 0.01 to 10% by weight, preferably from 0.05 to 5% by weight. In a case of an emulsifiable concentrate or a wettable powder, the proportion is selected suitably within a range of from 1 to 50% by weight, preferably from 5 to 20% by weight.

The dose of the herbicide of the present invention varies depending upon the type of the compound, the weeds to be controlled, the germination tendency, the environmental conditions and the type of the formulation to be used. However, in the case of a dust or a granule which is used by itself, the dose of the active ingredient is selected suitably within a range of from 0.1 g to 5 kg, preferably from 1 g to 1 kg, per 10 ares. In a case of an emulsifiable concentrate or a wettable powder which is used in a liquid state, the dose of the active ingredient is selected suitably within a range of from 1 to 50,000 ppm, preferably from 10 to 10,000 ppm.

Further, the compound of the present invention may be used in combination with an insecticide, a fungicide, other herbicide, a plant growth controlling agent, a fertilizer or the like, as the case requires.

Now, the formulation method will be described with reference to typical Formulation Examples. The compounds, types of the additives and blending ratios are not limited to such specific Examples and may be changed within wide ranges. In the following description, "parts" means "parts by weight".

FORMULATION EXAMPLE 1 (Wettable Powder)

To 10 parts by weight of Compound No. 172, 0.5 part of polyoxyethyleneoctylphenyl ether, 0.5 part of sodium naphthalene sulfonate-formalin condensate, 20 parts of diatomaceous earth and 69 parts of clay were mixed and pulverized to obtain a wettable powder.

FORMULATION EXAMPLE 2 (Wettable Powder)

To 10 parts of Compound No. 2, 0.5 part of polyoxyethyleneoctylphenyl ether, 0.5 part of sodium β-naphthalene sulfonate-formalin condensate, 20 parts of diatomaceous earth, 5 parts of fine silica and 64 parts of clay were mixed and pulverized to obtain a wettable powder.

FORMULATION EXAMPLE 3 (Wettable Powder)

To 10 parts of Compound No. 24, 0.5 part of polyoxyethyleneoctylphenyl ether, 0.5 part of sodium β-naphthalene sulfonate-formalin condensate, 20 parts of diatomaceous earth, 5 parts of fine silica and 64 parts of calcium carbonate, were mixed and pulverized to obtain a wettable powder.

FORMULATION EXAMPLE 4 (Emulsifiable Concentrate)

To 10 parts of Compound No. 9, 80 parts of a mixture comprising equal amounts of xylene and isophorone and 10 parts of a mixture comprising a polyoxyethylene sorbitol alkylate surfactant, a polyoxyethylenealkylaryl polymer and an alkylaryl sulfonate, were added, and the mixture was thoroughly stirred to obtain an emulsifiable concentrate.

FORMULATION EXAMPLE 5 (Granule)

1 part of Compound No. 168, 89 parts of a bulking agent comprising a 1:3 mixture of talc and bentonite, 5 parts of fine silica, 5 parts of a mixture comprising a polyoxyethylene sorbitol alkylate surfactant, a polyoxyethylenealkylaryl polymer and an alkylaryl sulfonate and 10 parts of water were mixed and thoroughly kneaded to obtain a paste, which was extruded from sieve apertures with a diameter of 0.7 mm. The extruded product was dried and then cut into a length of from 0.5 to 1 mm to obtain granules.

Now, the herbicidal effects of the compounds of the present invention will be described with reference to Test Examples.

TEST EXAMPLE 1 (Test on Herbicidal Effects by Paddy Field Soil Treatment)

In a plastic pot (surface area: 100 cm²) filled with paddy field soil, barnyardgrass (Eo), monochoria (Mo) and bulrush (Sc) were sown after puddling and leveling, and flooded to a water depth of 3 cm. Next day, a wettable powder prepared in accordance with Formulation Example 1 was diluted with water and applied dropwise to the water surface. The dose was 100 g of the active ingredient per ares. The plants were then cultured in a green house, and the evaluation of the herbicidal effects was conducted on the 21st day after the application in accordance with the standards as identified in Table 60. Further, as comparative compounds, compounds identified in Table 61 were formulated and used in the same manner. The results are shown in Tables 62-65.

                  TABLE 60                                                         ______________________________________                                                      Herbicidal effects                                                Index        (growth-controlling degree)                                       No.          or phytotoxicity                                                  ______________________________________                                         5            Herbicidal effect or phytotoxicity:                                            at least 90%                                                      4            Herbicidal effect or phytotoxicity:                                            at least 70% and less than 90%                                    3            Herbicidal effect or phytotoxicity:                                            at least 50% and less than 70%                                    2            Herbicidal effect or phytotoxicity:                                            at least 30% and less than 50%                                    1            Herbicidal effect or phytotoxicity:                                            at least 10 and less than 30%                                     0            Herbicidal effect or phytotoxicity:                                            0 to less than 10%                                                ______________________________________                                    

                  TABLE 61                                                         ______________________________________                                         Structural formulae    References                                              ______________________________________                                         Comparative compound A                                                          ##STR509##            Japanese Unexamined Patent Publication No.                                     121973/1990 Japanese Unexamined Patent Publication                             o. 56469/1990                                           Comparative compound B                                                          ##STR510##            Japanese Unexamined Patent Publication No.                                     121973/1990 Japanese Unexamined Patent Publication                             o. 56469/1990                                           Comparative compound C                                                          ##STR511##            Japanese Unexamined Patent Publication No.                                     121973/1990                                             Comparative compound D                                                          ##STR512##            Japanese Unexamined Patent Publication No.                                     121973/1990                                             Comparative compound E                                                          ##STR513##            Japanese Unexamined Patent Publication No.                                     121973/1990                                             Comparative compound F                                                          ##STR514##            Japanese Unexamined Patent Publication No.                                     121973/1990                                             ______________________________________                                    

                  TABLE 62                                                         ______________________________________                                         Compound    Herbicidal effect                                                  No.         Eo           Mo     Sc                                             ______________________________________                                          1          5            5      5                                               2          5            5      5                                               4          5            5      5                                               8          5            5      5                                               9          5            5      5                                              10          5            5      5                                              11          5            5      5                                              12          5            5      5                                              13          5            5      5                                              16          5            5      5                                              24          5            5      5                                              26          5            5      5                                              34          5            5      5                                              35          5            5      5                                              36          5            5      5                                              38          5            5      5                                              40          5            5      5                                              42          5            5      5                                              45          5            5      5                                              48          5            5      5                                              50          5            5      5                                              59          5            5      5                                              61          5            5      5                                              62          5            5      5                                              63          5            5      5                                              71          5            5      5                                              88          5            5      5                                              105         5            5      5                                              165         5            5      5                                              167         5            5      5                                              169         5            5      5                                              171         5            5      5                                              172         5            5      5                                              178         5            5      5                                              ______________________________________                                    

                  TABLE 63                                                         ______________________________________                                         Compound    Herbicidal effect                                                  No.         Eo           Mo     Sc                                             ______________________________________                                         182         5            5      5                                              262         5            5      5                                              286         5            5      5                                              301         5            5      5                                              365         5            5      5                                              405         5            5      5                                              445         5            5      5                                              505         5            5      5                                              506         5            5      5                                              507         5            5      5                                              508         5            5      5                                              509         5            5      5                                              511         5            5      5                                              512         5            5      5                                              515         5            5      4                                              516         5            5      4                                              519         5            5      5                                              520         5            5      5                                              522         5            5      5                                              523         5            5      5                                              524         5            5      5                                              525         5            5      5                                              526         5            5      5                                              527         5            5      5                                              528         5            5      5                                              529         5            5      5                                              530         5            5      5                                              531         5            5      5                                              533         5            5      5                                              535         5            5      5                                              539         5            5      5                                              541         5            5      5                                              542         5            5      5                                              543         5            5      5                                              ______________________________________                                    

                  TABLE 64                                                         ______________________________________                                         Compound    Herbicidal effect                                                  No.         Eo           Mo     Sc                                             ______________________________________                                         534         5            5      5                                              544         5            5      5                                              545         5            5      5                                              546         5            5      5                                              547         5            5      5                                              548         5            5      5                                              549         5            5      5                                              550         5            5      5                                              551         5            5      5                                              553         5            5      5                                              554         5            5      5                                              555         5            5      5                                              556         5            5      5                                              558         5            5      5                                              562         5            5      5                                              563         5            5      5                                              564         5            5      5                                              567         5            5      5                                              568         5            5      5                                              572         5            5      5                                              573         5            5      5                                              575         5            5      5                                              578         5            5      5                                              584         5            5      5                                              588         5            5      5                                              589         5            5      5                                              591         5            5      5                                              593         5            5      5                                              594         5            5      5                                              595         5            5      5                                              596         5            5      5                                              597         5            5      5                                              598         5            5      5                                              599         5            5      5                                              ______________________________________                                    

                  TABLE 65                                                         ______________________________________                                         Compound    Herbicidal effect                                                  No.         Eo           Mo     Sc                                             ______________________________________                                         600         5            5      5                                              611         5            5      5                                              613         5            5      5                                              614         5            5      5                                              615         5            5      5                                              616         5            5      5                                              619         5            5      5                                              622         5            5      5                                              626         5            5      5                                              628         5            5      4                                              665         5            5      5                                              671         5            5      5                                              681         5            5      5                                              693         5            5      5                                              770         3            5      5                                              772         5            5      5                                              787         5            5      5                                              789         5            5      5                                              797         5            5      5                                              813         5            5      5                                              815         5            5      5                                              831         5            5      5                                              834         5            3      5                                              929         5            5      5                                              931         5            5      5                                              933         5            5      5                                              952         5            5      5                                              955         5            5      5                                              Comparative 0            0      0                                              compound A                                                                     Comparative 4            1      2                                              compound B                                                                     Comparative 0            0      0                                              compound E                                                                     Comparative 0            0      0                                              compound F                                                                     ______________________________________                                    

TEST EXAMPLE 2 (Test on Herbicidal Effects by Upland Field Soil Treatment)

In a plastic pot (surface area: 120 cm²) filled with upland field soil, barnyardgrass (Ec), pale smartweed (Po), slender amaranth (Am), common lambsquarters (Ch) and rice flatsedge (Ci) were sown and covered with soil. A wettable powder prepared in accordance with Formulation Example 1 was diluted with water and applied uniformly to the soil surface by a small-sized sprayer in an amount of 100 l/10 ares so as to apply 100 g of the active ingredient per 10 ares. The plants were then cultured in a green house, and the evaluation of the herbicidal effects was conducted on the 21st day after the application in accordance with the standards as identified in Table 60. Further, as comparative compounds, compounds identified in Table 61 were formulated and used in the same manner. The results are shown in Tables 66-69.

                  TABLE 66                                                         ______________________________________                                         Compound  Herbicidal effect                                                    No.       Ec        Po    Am       Ch  Ci                                      ______________________________________                                          2        5         5     5        5   5                                        4        5         5     5        5   5                                        8        5         5     5        5   5                                        9        5         5     5        5   5                                       10        5         5     5        5   5                                       11        5         5     5        5   5                                       12        5         5     5        5   5                                       13        5         5     5        5   5                                       16        5         5     5        5   5                                       24        5         5     5        5   5                                       26        5         5     5        5   5                                       30        5         5     5        5   5                                       34        5         5     5        5   5                                       35        5         5     5        5   5                                       36        5         5     5        5   5                                       38        5         5     5        5   5                                       40        5         5     5        5   5                                       42        5         5     5        5   5                                       48        5         5     5        5   5                                       50        5         5     5        5   5                                       59        5         5     5        5   5                                       61        5         5     5        5   5                                       62        5         5     5        5   5                                       88        5         5     5        5   5                                       105       5         5     5        5   5                                       109       5         5     5        5   5                                       165       5         5     5        5   5                                       167       5         5     5        5   5                                       169       5         5     5        5   5                                       171       5         5     5        5   5                                       172       5         5     5        5   5                                       178       5         5     5        5   5                                       204       5         5     5        5   5                                       262       5         4     5        5   5                                       ______________________________________                                    

                  TABLE 67                                                         ______________________________________                                         Compound  Herbicidal effect                                                    No.       Ec        Po    Am       Ch  Ci                                      ______________________________________                                         286       5         5     5        5   5                                       301       4         5     5        5   5                                       386       5         5     5        5   5                                       506       5         5     5        5   5                                       507       4         5     5        5   5                                       508       5         5     5        5   5                                       509       4         5     5        5   4                                       511       5         5     5        5   5                                       512       5         5     5        5   5                                       519       5         5     5        5   5                                       520       5         5     5        5   5                                       522       5         5     5        5   5                                       523       5         5     5        5   5                                       524       5         5     5        5   5                                       525       5         5     5        5   5                                       526       5         5     5        5   5                                       528       5         5     5        5   5                                       529       5         5     5        5   5                                       530       5         5     5        5   5                                       531       5         5     5        5   5                                       533       5         5     5        5   5                                       537       4         5     5        5   5                                       539       5         5     5        5   5                                       541       5         5     5        5   5                                       543       5         5     5        5   5                                       544       5         5     5        5   5                                       546       5         5     5        5   5                                       547       5         5     5        5   5                                       548       5         5     5        5   5                                       549       5         5     5        5   5                                       550       5         5     5        5   5                                       551       5         5     5        5   5                                       553       5         5     5        5   5                                       554       5         5     5        5   5                                       ______________________________________                                    

                  TABLE 68                                                         ______________________________________                                         Compound  Herbicidal effect                                                    No.       Ec        Po    Am       Ch  Ci                                      ______________________________________                                         555       5         5     5        5   5                                       556       4         5     5        5   5                                       558       4         5     5        5   5                                       562       5         5     5        5   5                                       563       5         5     5        5   5                                       564       4         5     5        5   5                                       567       4         5     5        5   5                                       568       5         5     5        5   5                                       573       5         5     5        5   5                                       575       5         5     5        5   5                                       578       5         5     5        5   5                                       584       5         5     5        5   5                                       588       5         5     5        5   5                                       589       5         5     5        5   5                                       591       5         5     5        5   5                                       594       5         5     5        5   5                                       595       5         5     5        5   5                                       596       5         5     5        5   5                                       597       5         5     5        5   5                                       598       5         5     5        5   5                                       599       5         5     5        5   5                                       600       4         5     5        5   5                                       611       5         5     5        5   5                                       613       5         5     5        5   5                                       614       5         5     5        5   5                                       615       4         5     5        5   5                                       616       5         5     5        5   5                                       626       5         5     5        5   5                                       627       4         5     5        5   5                                       628       5         5     5        5   5                                       665       5         5     5        5   5                                       667       3         5     5        5   5                                       681       5         5     5        5   5                                       693       3         5     5        5   5                                       ______________________________________                                    

                  TABLE 69                                                         ______________________________________                                         Compound   Herbicidal effect                                                   No.        Ec        Po    Am      Ch  Ci                                      ______________________________________                                         770        3         5     5       5   5                                       772        5         5     5       5   5                                       787        5         5     5       5   5                                       789        5         5     5       5   5                                       797        3         5     5       5   5                                       815        5         5     5       5   5                                       831        3         5     5       5   5                                       834        3         5     5       5   5                                       852        2         5     5       5   5                                       883        3         5     5       3   5                                       929        4         5     4       4   5                                       931        5         5     5       4   5                                       933        5         5     5       5   5                                       952        5         4     5       5   5                                       984        4         5     5       5   5                                       Comparative                                                                               0         0     0       0   0                                       compound A                                                                     Comparative                                                                               0         0     2       3   0                                       compound B                                                                     Comparative                                                                               1         2     5       4   2                                       compound C                                                                     Comparative                                                                               0         2     4       4   1                                       compound D                                                                     Comparative                                                                               0         0     2       0   1                                       compound E                                                                     Comparative                                                                               0         0     0       0   0                                       compound F                                                                     ______________________________________                                    

TEST EXAMPLE 3 (Test on Herbicidal Effects by Upland Field Foliage Treatment)

In a plastic pot (surface area: 120 cm²) filled with upland field soil, barnyardgrass (Ec), pale smartweed (Po), slender amaranth (Am), common lambsquarters (Ch) and rice flatsedge (Ci) were sown and covered with soil and were cultured in a green house for 2 weeks. A wettable powder prepared in accordance with Formulation Example 1 was diluted with water and applied onto the entire foliages of the plants from above by a small-sized sprayer in an amount of 100 l/10 ares so as to apply 100 g of the active ingredient per 10 ares. The plants were then cultured in the green house, and the evaluation of the herbicidal effects was conducted on the 14th day after the treatment in accordance with the standards as identified in Table 60. Further, as comparative compounds, compounds identified in Table 61 were formulated and used in the same manner. The results are shown in Tables 70-74.

                  TABLE 70                                                         ______________________________________                                         Compound  Herbicidal effect                                                    No.       Ec        Po    Am       Ch  Ci                                      ______________________________________                                          1        5         5     5        5   5                                        2        5         5     5        5   5                                        4        5         5     5        5   5                                        8        5         5     5        5   5                                        9        5         5     5        5   5                                       10        5         5     5        5   5                                       11        5         5     5        5   5                                       12        5         5     5        5   5                                       13        5         5     5        5   5                                       16        5         5     5        5   5                                       24        5         5     5        5   5                                       26        5         5     5        5   5                                       30        5         5     5        5   5                                       34        5         5     5        5   5                                       35        5         5     5        5   5                                       36        5         5     5        5   5                                       38        5         5     5        5   5                                       40        5         5     5        5   5                                       42        5         5     5        5   5                                       48        5         5     5        5   5                                       59        5         5     5        5   5                                       61        5         5     5        5   5                                       62        5         5     5        5   5                                       71        5         5     5        5   5                                       88        5         5     5        5   5                                       105       5         5     5        5   5                                       159       3         5     5        4   5                                       162       5         5     5        5   5                                       165       5         5     5        5   5                                       167       5         5     5        5   5                                       169       5         5     5        5   5                                       171       5         5     5        5   5                                       178       5         5     5        5   5                                       204       5         5     5        5   5                                       ______________________________________                                    

                  TABLE 71                                                         ______________________________________                                         Compound  Herbicidal effect                                                    No.       Ec        Po    Am       Ch  Ci                                      ______________________________________                                         262       5         5     5        5   5                                       286       5         5     5        5   5                                       301       5         5     5        5   3                                       344       3         5     5        5   4                                       365       3         5     5        5   5                                       367       4         5     5        4   5                                       445       5         5     5        5   5                                       488       5         5     5        5   5                                       505       5         5     5        5   4                                       506       5         5     5        5   5                                       507       5         5     5        5   5                                       508       5         5     5        5   5                                       509       5         5     5        5   5                                       511       5         5     5        5   5                                       512       5         5     5        5   5                                       519       5         5     5        5   5                                       520       5         5     5        5   5                                       523       5         5     5        5   5                                       524       5         5     5        5   5                                       525       3         5     5        5   3                                       526       5         5     5        5   5                                       528       5         5     5        5   5                                       529       5         5     5        5   5                                       530       5         5     5        5   5                                       531       5         5     5        5   5                                       533       5         5     5        5   5                                       534       4         5     5        4   5                                       539       5         5     5        5   5                                       540       3         5     5        5   3                                       541       5         5     5        5   5                                       543       5         5     5        5   5                                       544       5         5     5        5   5                                       546       5         5     5        5   5                                       547       5         5     5        5   5                                       ______________________________________                                    

                  TABLE 72                                                         ______________________________________                                         Compound  Herbicidal effect                                                    No.       Ec        Po    Am       Ch  Ci                                      ______________________________________                                         548       5         5     5        5   5                                       549       5         5     5        5   5                                       550       5         5     5        5   5                                       551       5         5     5        5   5                                       553       5         5     5        5   5                                       554       5         5     5        4   5                                       555       5         5     5        3   5                                       556       4         5     5        4   5                                       558       5         5     5        5   5                                       562       5         5     5        5   5                                       563       5         5     5        5   5                                       564       5         5     5        5   5                                       567       5         5     5        5   5                                       568       5         5     5        5   5                                       573       5         5     5        5   5                                       575       5         5     5        5   5                                       578       5         5     5        5   5                                       584       5         5     5        5   5                                       588       5         5     5        5   5                                       589       5         5     5        5   5                                       591       5         5     5        5   5                                       594       5         5     5        5   5                                       595       5         5     5        5   5                                       596       5         5     5        5   5                                       597       5         5     5        5   5                                       598       5         5     5        5   5                                       599       5         5     5        5   5                                       600       5         5     5        5   5                                       611       5         5     5        5   5                                       613       5         5     5        5   5                                       614       5         5     5        5   5                                       615       5         5     5        5   5                                       616       5         5     5        5   5                                       619       4         5     5        5   5                                       ______________________________________                                    

                  TABLE 73                                                         ______________________________________                                         Compound  Herbicidal effect                                                    No.       Ec        Po    Am       Ch  Ci                                      ______________________________________                                         622       4         5     5        5   4                                       627       5         5     5        5   5                                       628       5         5     5        5   4                                       665       5         5     5        5   5                                       667       5         5     5        5   5                                       671       5         5     5        5   5                                       681       5         5     5        5   3                                       691       5         5     5        5   5                                       693       5         5     5        5   5                                       714       5         5     5        5   5                                       738       5         3     5        4   5                                       740       5         5     5        5   5                                       760       3         5     5        4   5                                       770       5         5     5        5   5                                       772       5         5     5        5   5                                       787       5         5     5        5   5                                       789       5         5     5        5   5                                       797       5         5     5        5   5                                       813       5         5     5        5   5                                       815       5         5     5        5   5                                       827       4         5     5        5   3                                       829       5         5     5        5   4                                       831       5         5     5        5   5                                       852       3         5     5        4   3                                       854       5         5     5        3   4                                       885       5         5     5        5   5                                       887       4         5     5        5   5                                       891       5         5     5        5   5                                       892       5         5     5        5   5                                       897       5         5     5        3   5                                       929       5         5     5        5   5                                       931       5         5     5        5   5                                       933       5         5     5        5   5                                       952       5         5     5        5   5                                       ______________________________________                                    

                  TABLE 74                                                         ______________________________________                                         Compound   Herbicidal effect                                                   No.        Ec        Po    Am      Ch  Ci                                      ______________________________________                                         955        5         5     5       5   5                                       683        5         5     5       5   5                                       984        5         5     5       5   5                                       958        5         5     5       5   5                                       Comparative                                                                               0         0     0       0   0                                       compound A                                                                     Comparative                                                                               0         2     3       3   0                                       compound B                                                                     Comparative                                                                               2         1     4       5   2                                       compound C                                                                     Comparative                                                                               0         1     2       4   0                                       compound D                                                                     Comparative                                                                               0         4     3       0   1                                       compound E                                                                     Comparative                                                                               0         0     0       0   0                                       compound F                                                                     ______________________________________                                    

TEST EXAMPLE 4 (Test on Crop Plant Selectivity by Paddy Field Soil Treatment)

In a 1/10,000a plastic pot, paddy field soil was filled, irrigated, paddled and leveled. Then, barnyardgrass (Eo), monochoria (Mo) and bulrush (Sc) were sown at a depth of 0.5 cm. Further, two seedlings of rice (Or) of 2.5 leaf stage was transplanted at a transplantation depth of 2 cm. Then, the pot was flooded to a water depth of 3 cm. Next day, a prescribed amount of the active ingredient (g^(ai) /10a) of a wettable powder prepared in accordance with Formulation Example 1 was diluted with water and applied dropwise to the water surface. The plants were then cultured in a green house, and the evaluation of the herbicidal effects and phytotoxicity was conducted on the 28th day after the application in accordance with the standards as identified in Table 60. Further, as comparative compounds, compounds identified in Table 61 were formulated and used in the same manner. The results are shown in Tables 75 to 77.

                  TABLE 75                                                         ______________________________________                                                            Herbicidal                                                  Compound                                                                               Dose       effect       Phytotoxicity                                  No.     (g.sup.ai /10a)                                                                           Eo    Mo     Sc  Or                                         ______________________________________                                          1      25         4     4      3   0                                           2      1.6        5     5      4   0                                           4      6.3        5     5      3   1                                           8      6.3        5     5      5   0                                           9      6.3        5     5      5   0                                           10     6.3        5     5      5   0                                           11     6.3        5     5      5   1                                           12     1.6        5     5      3   0                                           34     6.3        5     5      5   0                                           35     6.3        5     5      5   1                                           36     1.6        5     5      3   0                                           59     25         5     5      3   0                                          105     25         5     5      3   0                                          165     6.3        5     5      5   0                                          167     25         5     5      5   0                                          169     25         5     5      5   0                                          171     6.3        5     5      5   0                                          172     6.3        5     5      5   0                                          178     25         4     5      5   0                                          262     6.3        4     5      3   0                                          504     25         5     5      3   0                                          509     6.3        5     5      5   0                                          511     1.6        5     5      4   0                                          522     6.3        5     5      5   0                                          523     25         5     5      5   1                                          524     25         5     5      5   0                                          525     6.3        5     5      5   0                                          526     1.6        5     5      4   0                                          528     1.6        5     5      5   0                                          529     1.6        5     5      5   0                                          530     6.3        5     5      5   0                                          531     1.6        5     5      4   1                                          533     6.3        5     5      5   0                                          ______________________________________                                    

                  TABLE 76                                                         ______________________________________                                                            Herbicidal                                                  Compound                                                                               Dose       effect       Phytotoxicity                                  No.     (g.sup.ai /10a)                                                                           Eo    Mo     Sc  Or                                         ______________________________________                                         534     6.3        5     5      5   0                                          541     6.3        5     5      3   0                                          543     6.3        5     5      3   0                                          544     6.3        5     5      5   0                                          545     6.3        3     5      3   0                                          546     6.3        5     5      3   0                                          547     6.3        4     5      4   0                                          548     6.3        4     4      3   0                                          549     6.3        5     5      4   0                                          550     6.3        5     5      3   0                                          551     6.3        5     5      5   0                                          553     6.3        5     5      5   1                                          554     6.3        5     5      5   0                                          555     25         5     5      5   0                                          556     25         5     5      5   0                                          562     6.3        5     5      5   1                                          563     25         5     5      5   0                                          568     25         3     5      5   0                                          572     25         4     5      4   0                                          573     25         5     5      5   0                                          578     25         5     5      5   1                                          600     25         4     5      3   1                                          611     6.3        5     5      3   1                                          613     6.3        5     5      4   0                                          614     6.3        4     5      3   0                                          616     6.3        5     5      5   0                                          623     6.3        4     5      5   0                                          681     25         5     5      4   1                                          797     6.3        4     5      3   0                                          831     6.3        5     5      5   0                                          929     6.3        5     5      5   0                                          931     25         5     5      5   0                                          933     25         4     5      5   1                                          ______________________________________                                    

                  TABLE 77                                                         ______________________________________                                                            Herbicidal                                                  Compound Dose      effect       Phytotoxicity                                  No.      (g.sup.ai /10a)                                                                          Eo    Mo     Sc  Or                                         ______________________________________                                         955      25        4     5      5   1                                          Comparative                                                                    compound A                                                                              25        0     0      0   0                                          Comparative                                                                             25        2     0      0   0                                          compound B                                                                     Comparative                                                                             25        3     4      3   4                                          compound C                                                                     Comparative                                                                             25        2     3      1   3                                          compound D                                                                     Comparative                                                                             100       0     0      0   0                                          compound E                                                                     Comparative                                                                             100       0     0      0   0                                          compound F                                                                     ______________________________________                                    

TEST EXAMPLE 5 (Test on Crop Plant Selectivity by Upland Field Soil Treatment)

In a plastic pot (surface area: 600 cm²) filled with upland field soil, wheat (Tr), barnyardgrass (Ec), green foxtail (Se), Johnsongrass (So), Alopecurus myosuroides (Al), pale smartweed (Po), slender amaranth (Am) and common lambsquarters (Ch) were sown and covered with soil. Next day, a prescribed amount of the active ingredient (g^(ai) /10a) of a wettable powder prepared in accordance with Formulation Example 1 was diluted with water and applied uniformly to the soil surface by a small-sized sprayer in an amount of 100 l per 10 ares. The plants were then cultured in a green house, and the evaluation of the herbicidal effects was conducted on the 21st day after the application in accordance with the standards as identified in Table 60. Further, as comparative compounds, compounds identified in Table 61 were formulated and used in the same manner. The results are shown in Tables 78 to 79.

                  TABLE 78                                                         ______________________________________                                                                             Phyto-                                     Compound                                                                               Dose     Herbicidal effect  toxicity                                   No.     (g.sup.ai /10a)                                                                         Ec    Se  So  Al  Po  Am   Ch  Tr                             ______________________________________                                          2      25       5     5   5   5   5   5    5   1                               4      25       5     5   5   5   5   5    5   1                               9      25       5     5   5   5   5   5    5   1                               10     25       5     5   5   5   5   5    5   1                               11     25       5     4   5   5   5   5    5   0                               12     25       5     5   5   5   5   5    5   1                               13     25       4     3   5   5   5   5    5   0                               24     25       5     4   5   5   5   5    5   0                               26     25       5     4   5   5   5   5    5   0                               40     25       4     5   5   3   5   5    5   0                               42     25       3     1   4   3   5   5    5   0                               61     25       5     5   5   5   5   5    3   0                               62     6.3      5     4   5   5   5   5    3   0                              507     25       5     5   5   5   5   5    5   0                              511     25       5     3   5   5   5   5    3   0                              512     6.3      5     3   5   5   5   5    5   0                              523     25       5     3   4   4   5   5    5   1                              525     6.3      5     3   5   5   5   5    5   0                              526     6.3      5     5   5   5   5   5    5   1                              527     6.3      5     5   5   5   5   5    5   0                              529     25       5     5   5   5   5   5    5   0                              531     25       5     5   5   5   5   5    5   0                              536     6.3      5     3   5   5   5   5    5   0                              ______________________________________                                    

                  TABLE 78                                                         ______________________________________                                                                              Phyto-                                    Compound Dose     Herbicidal effect  toxicity                                  No.      (g.sup.ai /10a)                                                                         Ec    Se  So  Al  Po  Am   Ch  Tr                            ______________________________________                                         553      25       5     5   5   5   5   5    5   0                             554      25       5     5   5   5   5   5    5   0                             563      6.3      5     4   5   5   5   5    5   0                             591      6.3      3     4   5   5   5   5    5   0                             665      6.3      3     3   4   4   5   5    5   0                             787      6.3      3     5   5   5   5   5    5   3                             789      6.3      2     3   5   5   5   5    5   2                             Comparative                                                                             25       0     0   0   0   0   0    0   0                             compound A                                                                     Comparative                                                                             25       0     0   0   0   0   1    1   0                             compound B                                                                     Comparative                                                                             100      1     0   1   1   2   5    4   3                             compound C                                                                     Comparative                                                                             400      2     1   3   2   2   5    5   4                             compound D                                                                     Comparative                                                                             25       0     0   0   0   0   0    0   0                             compound E                                                                     Comparative                                                                             25       0     0   0   0   0   0    0   0                             compound F                                                                     ______________________________________                                    

TEST EXAMPLE 6 (Test on Crop Plant Selectivity by Upland Field Foliage Treatment)

In a plastic pot (surface area: 600 cm²) filled with upland field soil, rice (Or), wheat (Tr), barnyardgrass (Ec), Johnsongrass (So), Alopecurus myosucroides (Al), pale smartweed (Po), slender amaranth (Am) and common lambsquarters (Ch) were sown and cultured in a green house for 2 weeks. Then, a prescribed amount of the active ingredient (g^(ai) /10a) of a wettable powder prepared in accordance with Formulation Example 1 was diluted with water and applied onto the entire foliages of the plants from above by a small-sized sprayer in an amount of 100 l per 10 ares. The plants were then cultured in a green house, and the evaluation of the herbicidal effects was conducted on the 14th day after the treatment in accordance with the standards as identified in Table 60. Further, as comparative compounds, compounds identified in Table 61 were formulated and used in the same manner. The results are shown in Tables 80 and 81.

                  TABLE 80                                                         ______________________________________                                                                              Phyto-                                    Compound                                                                               Dose     Herbicidal effect   toxicity                                  No.     (g.sup.ai /10a)                                                                         Ec    So  Al  Po  Am   Ch   Or  Tr                            ______________________________________                                          2      25       5     5   5   5   5    5    1   1                              4      25       5     5   5   5   5    5    0   0                              8      25       5     4   5   5   5    5    1   0                              9      25       5     5   5   5   5    5    0   0                              24     25       5     5   5   5   5    5    2   0                              26     25       5     5   5   5   5    5    1   0                              34     25       5     5   5   5   5    5    0   0                              35     25       5     5   5   5   5    5    0   0                              40     25       3     4   3   5   5    4    1   0                              42     25       3     3   3   4   4    4    1   0                              61     1.6      5     5   5   5   5    3    1   0                              62     25       5     5   5   5   5    5    0   0                             171     25       5     5   5   5   5    5    1   0                             262     25       5     5   4   4   5    3    0   0                             506     6.3      5     5   5   5   5    4    1   0                             507     6.3      5     5   5   5   5    3    1   0                             509     6.3      5     5   5   5   5    5    1   0                             511     25       5     5   5   5   5    5    2   0                             512     25       5     5   5   5   5    5    2   0                             522     25       5     5   5   5   5    5    2   0                             526     25       5     5   5   5   5    5    1   1                             527     6.3      5     5   5   5   5    5    1   0                             528     25       5     5   5   5   5    5    2   0                             529     6.3      5     5   5   5   5    5    1   0                             530     6.3      5     5   5   5   5    5    2   1                             531     1.6      5     5   5   5   5    5    1   0                             543     25       5     4   5   5   5    4    1   0                             547     6.3      5     5   5   5   5    4    2   0                             548     6.3      5     5   5   4   5    4    2   1                             549     6.3      5     5   5   5   5    5    0   0                             550     6.3      5     5   5   5   5    5    0   0                             551     6.3      5     5   5   5   5    5    2   0                             562     6.3      5     5   5   5   5    5    0   0                             ______________________________________                                    

                  TABLE 81                                                         ______________________________________                                                                               Phyto-                                   Compound Dose     Herbicidal effect   toxicity                                 No.      (g.sup.ai /10a)                                                                         Ec    So  Al  Po  Am   Ch  Or    Tr                          ______________________________________                                         563      25       5     5   5   5   5    5   0     0                           567      25       5     5   5   5   5    4   1     0                           568      25       5     5   5   5   5    5   0     0                           578      6.3      5     5   5   5   5    4   1     1                           597      1.6      4     3   5   5   5    5   1     1                           848      25       2     3   5   5   5    5   1     0                           929      25       5     5   5   5   5    5   1     0                           Comparative                                                                             25       0     0   0   0   0    0   0     0                           compound A                                                                     Comparative                                                                             25       0     0   0   1   2    1   1     0                           compound B                                                                     Comparative                                                                             100      2     2   1   1   4    5   4     2                           compound C                                                                     Comparative                                                                             400      0     0   0   5   4    5   3     3                           compound D                                                                     Comparative                                                                             100      0     0   0   0   0    0   0     0                           compound E                                                                     Comparative                                                                             100      0     0   0   0   0    0   0     0                           compound F                                                                     ______________________________________                                     

We claim:
 1. A condensed heterocyclic derivative of the formula (I): ##STR515## wherein: A is a heterocyclic ring of the formula ##STR516## R is a hydrogen atom; a hydroxyl group; an alkoxy group which may be substituted with pentanoyloxy, butanoyloxy, hexanoyloxy, ethoxycarbonyl, ethoxy, ethylmalonyl, benzoyloxy, (2'-trimethylsilyl)ethyl, methoxy, trimethylsilyl or (2'-methoxy)ethoxy; a benzyloxy group which may be substituted with methoxy; a phenyloxy group; a C₁ -C₂ alkylthio group; a benzylthio group; a phenylthio group; a C₃ -alkenyloxy group which may be substituted with Br; a C₃ -alkynyloxy group; a C₃ -alkenylthio group; a C₃ -alkynylthio group; a C₃ -alkylideneaminoxy group; O⁻ [N(CH₂ CH₂ CH₂ CH₄)₄ ]⁺ ; O⁻ (CH₃)₂ CHNH₃ ⁺ ; O⁻ CH₃ CH₂ CH₂ NH₃ ⁺ ; O⁻ Na⁺ ; or a group of the formula --NR⁶ R⁷, wherein:each of R⁶ and R⁷, which may be the same or different, is a hydrogen atom, a C₁ -C₄ alkyl group, a benzyl group, a phenyl group, a methylsulfonyl group or a phenylsulfonyl group; or R⁶ and R⁷ may, together with the nitrogen atom, form a 1,3-imidazole ring, pyrrolidine ring, piperidine ring or morpholine ring; each of R¹ and R², which may be the same or different, is a hydrogen atom; a formyl group; a C₁ -C₈ alkylcarbonyl group which may be substituted with fluorine; a cyclopentylcarbonyl group; a benzoyl group which may be substituted with chlorine; a pyridylcarbonyl group which may be substituted with methylsulfonyl; a carboxyl group; a group of the formula --CONR⁶ R⁷ ; a C₁ -C₈ alkylthiocarbonyl group which may be substituted with diethylamino; a C₃ -C₈ cycloalkylthiocarbonyl group; a phenyloxycarbonyl group which may be substituted with chlorine or methoxy; a C₁ -C₈ alkoxycarbonyl group which may be substituted with fluorine, chlorine, bromine, 2-furyl, 2-thienyl, cyano, ethoxycarbonyl, hydroxy, dimethylamino, cyclopropyl, methoxy, ethoxy or methylthio; a C₃ -cycloalkyl group; a C₁ -C₈ alkyl group which may be substituted with fluorine, chlorine, methoxy, nitro, cyano, methoxycarbonyl, dimethylamino or hydroxy; a C₂ -C₃ alkenyl group which may be substituted with CN or nitro; a C₃ alkynyl group; an ethoxy group; a methoxy group; a phenyl group which may be substituted with chlorine; a halogen atom; a benzyloxycarbonyl group which may be substituted with methoxy; a benzylthiocarbonyl group; a C₃ -C₈ cycloalkoxycarbonyl group; a phenylthiocarbonyl group; a C₃ -C₆ alkenyloxycarbonyl group which may be substituted with chlorine; a C₃ -C₆ alkynyloxycarbonyl group; a C₃ -C₆ alkenylthiocarbonyl group; a C₃ -C₆ alkynylthiocarbonyl group; an isopropylideneaminoxycarbonyl group; a nitro group; a cyano group; a halogenated carbonyl group; a group of the formula CR⁸ ═N--R⁹ ; a group of the formula NR¹⁰ R¹¹ or a group of the formula N═CR¹² R¹³, wherein:R⁶ and R⁷ are as defined above; R⁸ is a hydrogen atom, a phenyl group, or a methyl group; R⁹ is a hydroxyl group, a propyl group, a phenyl group, a benzyl group, a benzyloxy group, a methoxy group, a propoxy group, a propenyloxy group, a propynyloxy group, a phenoxy group, a methylamino group, a dimethylamino group, a phenylamino group or a phenylsulfonylamino group which may be substituted with methyl; each of R¹⁰ and R¹¹, which may be the same or different, is a hydrogen atom, a methyl group, a phenyl group, a benzyl group, a formyl group, an acetyl group, a benzoyl group, a pyridylcarbonyl group, an ethoxycarbonyl group, a methylsulfonyl group, a phenylsulfonyl group, a carbamoyl group, an ethylthiocarbonyl group or a phenylthiocarbonyl group which may be substituted with chlorine, or R¹⁰ and R¹¹ may, together with the nitrogen atom, form a morpholine ring; and each of R¹² and R¹³, which may be the same or different, is a hydrogen atom, a methyl group or a phenyl group, or R¹² and R¹³ may, together with the carbon atom to which they are bound, form a cyclopentylidene group; each of R³ and R⁴, which may be the same or different, is a hydrogen atom; a methoxy group which may be substituted with fluorine; a halogen atom; a methylamino group; a dimethylamino group or a C₁ -C₆ alkyl group; R⁵ is a hydrogen atom; a methyl group which may be substituted with methoxycarbonyl, ethoxycarbonyl, t-butylcarbonyloxy or methoxy; a formyl group; a C₁ -C₈ alkylcarbonyl group; a benzoyl group which may be substituted with chlorine; a pyridylcarbonyl group; a carbamoyl group; a C₂ -C₄ alkoxycarbonyl group; a phenyloxycarbonyl group; a benzyloxycarbonyl group; a methylthiocarbonyl group; a phenylthiocarbonyl group; a methylsulfonyl group; a p-tolylsulfonyl group; a tri-C₁ -C₄ -alkylsilyl group; a propenyl group; a propynyl group; a 4,6-dimethoxypyridin-2-yl group or a trichloromethylthio group; each of a, b, d and e is a nitrogen atom or a methine group, provided that at least two of them are nitrogen atoms; Y is a halogen atom, a methyl group, a methoxy group, a phenyl group, a nitro group, a methylamino group or a dimethylamino group, n is an integer of from 0 to 2, provided that when n is 2, it may represent a combination of different groups, W is an oxygen atom, a sulfur atom, an N-formyl group, a methylene group, a carbonyl group, a cyanomethylene group, and Z is a methine group;or a salt thereof.
 2. A pyrimidine derivative or a salt thereof according to claim 1, wherein A in the formula (I) is (A-4).
 3. A pyrimidine derivative or a salt thereof according to claim 1, wherein A in the formula (I) is (A-5), (A-6), (A-7), (A-8), (A-9) or (A-10).
 4. A pyrimidine derivative or a salt thereof according to claim 1, wherein A in the formula (I) is (A-13).
 5. A pyrimidine derivative or a salt thereof according to claim 1, wherein A in the formula (I) is (A-4), W is an oxygen atom or a sulfur atom, and each of R³ and R⁴ is an alkoxy group having 1 to 6 carbon atoms.
 6. A pyrimidine derivative or a salt thereof according to claim 1, wherein A in the formula (I) is (A-5), (A-6), (A-7), (A-8), (A-9) or (A-10), W is an oxygen atom or a sulfur atom, and each of R³ and R⁴ is an alkoxy group having 1 to 6 carbon atoms.
 7. A pyrimidine derivative or a salt thereof according to claim 1, wherein A in the formula (I) is (A-13), W is an oxygen atom or a sulfur atom, and each of R³ and R⁴ is an alkoxy group having 1 to 6 carbon atoms.
 8. A pyrimidine derivative according to claim 1, selected from the group consisting of:5-(4,6-dimethoxypyrimidin-2-yl)oxy-3-methoxycarbonyl-2-methylindol-4-carboxylic acid, and 5-(4,6-dimethoxypyrimidin-2-yl)oxy-2-methylindol-4-carboxylic acid.
 9. An herbicidal composition containing an herbicidally effective amount of the pyrimidine derivative of claim 1 and a carrier therefor.
 10. A condensed heterocyclic derivative of the formula (I): ##STR517## wherein: A is a heterocyclic ring of the formula ##STR518## R is a hydrogen atom; a hydroxyl group; an alkoxy group which may be substituted with pentanoyloxy, butanoyloxy, hexanoyloxy, ethoxycarbonyl, ethoxy, ethylmalonyl, benzoyloxy, (2'-trimethylsilyl)ethyl, methoxy, trimethylsilyl or (2'-methoxy)ethoxy; a benzyloxy group which may be substituted with methoxy; a phenyloxy group; a C₁ -C₂ alkylthio group; a benzylthio group; a phenylthio group; a C₃ -alkenyloxy group which may be substituted with Br; a C₃ -alkynyloxy group; a C₃ -alkenylthio group; a C₃ -alkynylthio group; a C₃ -alkylideneaminoxy group; O⁻ [N(CH₂ CH₂ CH₂ CH₃)₄ ]⁺ ; O⁻ (CH₃)₂ CHNH₃ ⁺ ; O⁻ CH₃ CH₂ CH₂ NH₃ ⁺ ; O⁻ Na⁺ ; or a group of the formula --NR⁶ R⁷, wherein:each of R⁶ and R⁷, which may be the same or different, is a hydrogen atom, a C₁ -C₄ alkyl group, a benzyl group, a phenyl group, a methylsulfonyl group or a phenylsulfonyl group; or R⁶ and R⁷ may, together with the nitrogen atom, form a 1,3-imidazole ring, pyrrolidine ring, piperidine ring or morpholine ring; each of R¹ and R², which may be the same or different, is a hydrogen atom; a formyl group; a C₁ -C₈ alkylcarbonyl group which may be substituted with fluorine; a cyclopentylcarbonyl group; a benzoyl group which may be substituted with chlorine; a pyridylcarbonyl group which may be substituted with methylsulfonyl; a carboxyl group; a group of the formula --CONR⁶ R⁷ ; a C₁ -C₈ alkylthiocarbonyl group which may be substituted with diethylamino; a C₃ -C₈ cycloalkylthiocarbonyl group; a phenyloxycarbonyl group which may be substituted with chlorine or methoxy; a C₁ -C₈ alkoxycarbonyl group which may be substituted with fluorine, chlorine, bromine, 2-furyl, 2-thienyl, cyano, ethoxycarbonyl, hydroxy, dimethylamino, cyclopropyl, methoxy, ethoxy or methylthio; a C₃ -cycloalkyl group; a C₁ -C₈ alkyl group which may be substituted with fluorine, chlorine, methoxy, nitro, cyano, methoxycarbonyl, dimethylamino or hydroxy; a C₂ -C₃ alkenyl group which may be substituted with CN or nitro; a C₃ alkynyl group; an ethoxy group; a methoxy group; a phenyl group which may be substituted with chlorine; a halogen atom; a benzyloxycarbonyl group which may be substituted with methoxy; a benzylthiocarbonyl group; a C₃ -C₈ cycloalkoxycarbonyl group; a phenylthiocarbonyl group; a C₃ -C₆ alkenyloxycarbonyl group which may be substituted with chlorine; a C₃ -C₆ alkynyloxycarbonyl group; a C₃ -C₆ alkenylthiocarbonyl group; a C₃ -C₆ alkynylthiocarbonyl group; an isopropylideneaminoxycarbonyl group; a nitro group; a cyano group; a halogenated carbonyl group; a group of the formula CR⁸ ═N--R⁹ ; a group of the formula NR¹⁰ R¹¹ or a group of the formula N═CR¹² R¹³, wherein:R⁶ and R⁷ are as defined above; R⁸ is a hydrogen atom, a phenyl group, or a methyl group; R⁹ is a hydroxyl group, a propyl group, a phenyl group, a benzyl group, a benzyloxy group, a methoxy group, a propoxy group, a propenyloxy group, a propynyloxy group, a phenoxy group, a methylamino group, a dimethylamino group, a phenylamino group or a phenylsulfonylamino group which may be substituted with methyl; each of R¹⁰ and R¹¹, which may be the same or different, is a hydrogen atom, a methyl group, a phenyl group, a benzyl group, a formyl group, an acetyl group, a benzoyl group, a pyridylcarbonyl group, an ethoxycarbonyl group, a methylsulfonyl group, a phenylsulfonyl group, a carbamoyl group, an ethylthiocarbonyl group or a phenylthiocarbonyl group which may be substituted with chlorine, or R¹⁰ and R¹¹ may, together with the nitrogen atom, form a morpholine ring; and each of R¹² and R¹³, which may be the same or different, is a hydrogen atom, a methyl group or a phenyl group, or R¹² and R¹³ may, together with the carbon atom to which they are bound, form a cyclopentylidene group; each of R³ and R⁴ which may be the same or different, is a hydrogen atom; a methoxy group which may be substituted with fluorine; a halogen atom; a methylamino group; a dimethylamino group or a C₁ -C₆ alkyl group; Y is a halogen atom, a methyl group, a methoxy group, a phenyl group, a nitro group, a methylamino group or a dimethylamino group, n is an integer of from 0 to 2, provided that when n is 2, it may represent a combination of different groups, W is an oxygen atom, a sulfur atom, an N-formyl group, a methylene group, a carbonyl group, a cyanomethylene group, and Z is a methine group;or a salt thereof.
 11. A pyrimidine derivative or a salt thereof according to claim 10, wherein each of R³ and R⁴ is an alkoxy group having 1 to 6 carbon atoms.
 12. A condensed heterocyclic derivative of the formula (I): ##STR519## wherein: A is a heterocyclic ring of the formula ##STR520## R is a hydrogen atom; a hydroxyl group; an alkoxy group which may be substituted with pentanoyloxy, butanoyloxy, hexanoyloxy, ethoxycarbonyl, ethoxy, ethylmalonyl, benzoyloxy, (2'-trimethylsilyl)ethyl, methoxy, trimethylsilyl or (2'-methoxy) ethoxy; a benzyloxy group which may be substituted with methoxy; a phenyloxy group; a C₁ -C₂ alkylthio group; a benzylthio group; a phenylthio group; a C₃ -alkenyloxy group which may be substituted with Br; a C₃ -alkynyloxy group; a C₃ -alkenylthio group; a C₃ -alkynylthio group; a C₃ -alkylideneaminoxy group; O⁻ [N(CH₂ CH₂ CH₂ CH₃)₄ ]⁺ ; O⁻ (CH₃)₂ CHNH₃ ⁺ ; O⁻ CH₃ CH₂ CH₂ NH₃ ⁺ ; O⁻ Na⁺ ; or a group of the formula --NR⁶ R⁷, wherein:each of R⁶ and R⁷, which may be the same or different, is a hydrogen atom, a C₁ -C₄ alkyl group, a benzyl group, a phenyl group, a methylsulfonyl group or a phenylsulfonyl group; or R⁶ and R⁷ may, together with the nitrogen atom, form a 1,3-imidazole ring, pyrrolidine ring, piperidine ring or morpholine ring; X¹ is a methylene group or a group of the formula NR¹⁴, X² is an oxygen atom, a sulfur atom, a methylene group, a group of the formula NR¹⁴, a carbonyl group, a group of the formula C═NOR¹⁵ or a hydroxymethylene group, such that when X¹, is a methylene group, X², is an oxygen atom, a sulfur atom, a carbonyl group or a group of the formula C═NRO¹⁵ ; and when X¹ is a group of the formula NR¹⁴, X² is an oxygen atom, a sulfur atom or a group of the formula NR¹⁴, wherein:R¹⁴ is a hydrogen atom or a methyl group, and R¹⁵ is a methyl group, each of Q² and Q³, which may be the same or different, is a group of the formula C<R¹⁸ R¹⁹, wherein:each of R¹⁸ and R¹⁹, which may be the same or different, is a hydrogen atom, a C₁ -C₂ alkyl group or a methoxycarbonylmethyl group, or R¹⁸ and R¹⁹ together form a carbonyl group or a group of the formula C═CHR²⁰, wherein: R²⁰ is a hydrogen atom or a methyl group, and Y is a halogen atom, a methyl group, a methoxy group, a phenyl group, a nitro group, a methylamino group or a dimethylamino group, n is an integer of from 0 to 2, provided that when n is 2, it may represent a combination of different groups, W is an oxygen atom, a sulfur atom, an N-formyl group, a methylene group, a carbonyl group, a cyanomethylene group, and Z is a methine group;or a salt thereof.
 13. A pyrimidine derivative or a salt thereof according to claim 12, wherein each of R³ and R⁴ is an alkoxy group having 1 to 6 carbon atoms.
 14. The condensed heterocyclic derivative of claim 12, wherein X¹ is an oxygen atom or a sulfur atom.
 15. A condensed heterocyclic derivative of the formula (I): ##STR521## wherein: A is a heterocyclic ring of the formula ##STR522## R is a hydrogen atom; a hydroxyl group; an alkoxy group which may be substituted with pentanoyloxy, butanoyloxy, hexanoyloxy, ethoxycarbonyl, ethoxy, ethylmalonyl, benzoyloxy, (2'-trimethylsilyl)ethyl, methoxy, trimethylsilyl or (2'-methoxy)ethoxy; a benzyloxy group which may be substituted with methoxy; a phenyloxy group; a C₁ -C₂ alkylthio group; a benzylthio group; a phenylthio group; a C₃ -alkenyloxy group which may be substituted with Br; a C₃ -alkynyloxy group; a C₃ -alkenylthio group; a C₃ -alkynylthio group; a C₃ -alkylideneaminoxy group; O⁻ [N(CH₂ CH₂ CH₂ CH₃)₄ ]⁺ ; O⁻ (CH₃)₂ CHNH₃ ⁺ ; O⁻ CH₃ CH₂ CH₂ NH₃ ⁺ ; O⁻ Na⁺ ; or a group of the formula --NR⁶ R⁷, whereineach of R⁶ and R⁷, which may be the same or different, is a hydrogen atom, a C₁ -C₄ alkyl group, a benzyl group, a phenyl group, a methylsulfonyl group or a phenylsulfonyl group; or R⁶ and R⁷ may, together with the nitrogen atom, form a 1,3-imidazole ring, pyrrolidine ring, piperidine ring or morpholine ring; one of R¹ and R² is a hydrogen atom; a formyl group; a C₁ -C₈ alkylcarbonyl group which may be substituted with fluorine; a cyclopentylcarbonyl group; a benzoyl group which may be substituted with chlorine; a pyridylcarbonyl group which may be substituted with methylsulfonyl; a carboxyl group; a group of the formula --CONR⁶ R⁷ ; a C₁ -C₈ alkylthiocarbonyl group which may be substituted with diethylamino; a C₃ -C₈ cycloalkylthiocarbonyl group; a phenyloxycarbonyl group which may be substituted with chlorine or methoxy; a C₁ -C₈ alkoxycarbonyl group which may be substituted with fluorine, chlorine, bromine, 2-furyl, 2-thienyl, cyano, ethoxycarbonyl, hydroxy, dimethylamino, cyclopropyl, methoxy, ethoxy or methlythio; a C₃ -cycloalkyl group; a C₁ -C₈ alkyl group which may be substituted with fluorine, chlorine, methoxy, nitro, cyano, methoxycarbonyl, dimethylamino or hydroxy; a C₂ -C₃ alkenyl group which may be substituted with CN or nitro; a C₃ alkynyl group; an ethoxy group; a methoxy group; a phenyl group which may be substituted with chlorine; a halogen atom; a benzyloxycarbonyl group which may be substituted with methoxy; a benzylthiocarbonyl group; a C₃ -C₈ cycloalkoxycarbonyl group; a phenylthiocarbonyl group; a C₃ -C₆ alkenyloxycarbonyl group which may be substituted with chlorine; a C₃ -C₆ alkynyloxycarbonyl group; a C₃ -C₆ alkenylthiocarbonyl group; a C₃ -C₆ alkynylthiocarbonyl group; an isopropylideneaminoxycarbonyl group; a nitro group; a cyano group; a halogenated carbonyl group; a group of the formula CR⁸ ═N--R⁹ ; a group of the formula NR¹⁰ R¹¹ or a group of the formula N═CR¹² R¹³, wherein:R⁶ and R⁷ are as defined above; R⁸ is a hydrogen atom, a phenyl group, or a methyl group; R⁹ is a hydroxyl group, a propyl group, a phenyl group, a benzyl group, a benzyloxy group, a methoxy group, a propoxy group, a propenyloxy group, a propynyloxy group, a phenoxy group, a methylamino group, a dimethylamino group, a phenylamino group or a phenylsulfonylamino group which may be substituted with methyl; each of R¹⁰ and R¹¹, which may be the same or different, is a hydrogen atom, a methyl group, a phenyl group, a benzyl group, a formyl group, an acetyl group, a benzoyl group, a pyridylcarbonyl group, an ethoxycarbonyl group, a methylsulfonyl group, a phenylsulfonyl group, a carbamoyl group, an ethylthiocarbonyl group or a phenylthiocarbonyl group which may be substituted with chlorine, or R¹⁰ and R¹¹ may, together with the nitrogen atom, form a morpholine ring; and each of R¹² and R¹³, which may be the same or different, is a hydrogen atom, a methyl group or a phenyl group, or R¹² and R¹³ may, together with the carbon atom to which they are bound, form a cyclopentylidene group; the other of R¹ and R² is a C₁ -C₈ alkylcarbonyl group which may be substituted with fluorine; a cyclopentylcarbonyl group; a benzoyl group which may be substituted with chlorine; a pyridylcarbonyl group which may be substituted with methylsulfonyl; a carboxyl group; a group of the formula --CONR⁶ R⁷ ; a C₁ -C₈ alkylthiocarbonyl group which may be substituted with diethylamino; a C₃ -C₈ cycloalkylthiocarbonyl group; a phenyloxycarbonyl group which may be substituted with chlorine or methoxy; a C₁ -C₈ alkoxycarbonyl group which may be substituted with fluorine, chlorine, bromine, 2-furyl, 2-thienyl, cyano, ethoxycarbonyl, hydroxy, dimethylamino, cyclopropyl, methoxy, ethoxy or methlythio; a benzyloxycarbonyl group which may be substituted with methoxy; a benzylthiocarbonyl group; a C₃ -C₈ cycloalkoxycarbonyl group; a phenylthiocarbonyl group; a C₃ -C₆ alkenyloxycarbonyl group which may be substituted with chlorine; a C₃ -C₆ alkynyloxycarbonyl group; a C₃ -C₆ alkenylthiocarbonyl group; a C₃ -C₆ alkynylthiocarbonyl group; an isopropylideneaminoxycarbonyl group; a cyano group; a halogenated carbonyl group; a group of the formula CR⁸ ═N--R⁹ ; a group of the formula NR¹⁰ R¹¹ or a group of the formula N═CR¹² R¹³ ; each of R³ and R⁴, which may be the same or different, is a hydrogen atom; a methoxy group which may be substituted with fluorine; a halogen atom; a methylamino group; a dimethylamino group or a C₁ -C₆ alkyl group; Y is a halogen atom, a methyl group, a methoxy group, a phenyl group, a nitro group, a methylamino group or a dimethylamino group, n is an integer of from 0 to 2, provided that when n is 2, it may represent a combination of different groups, W is an oxygen atom, a sulfur atom, an N-formyl group, a methylene group, a carbonyl group, a cyanomethylene group, and Z is a methine group;or a salt thereof.
 16. An herbicidal composition containing an herbicidally effective amount of the pyrimidine derivative of claim 15 and a carrier therefor.
 17. A pyrimidine derivative or a salt thereof according to claim 15, wherein each of R³ and R⁴ is an alkoxy group having 1 to 6 carbon atoms.
 18. A pyrimidine derivative according to claim 15, selected from the group consisting of:5-(4,6-dimethoxypyrimidin-2-yl)oxy-3-isopropoxycarbonyl-2-methylbenzofuran-4-carboxylic acid, 5-(4,6-dimethoxypyrimidin-2-yl)oxy-3-propoxycarbonyl-2-methylbenzofuran-4-carboxylic acid, 5-(4,6-dimethoxypyrimidin-2-yl)oxy-3-methoxycarbonyl-2-methylbenzofuran-4-carboxylic acid, 5-(4,6-dimethoxypyrimidin-2-yl)oxy-3-(2-fluoroethoxy)carbonyl-2-methylbenzofuran-4-carboxylic acid, 5-(4,6-dimethoxypyrimidin-2-yl)oxy-3-propargyloxycarbonyl-2-methylbenzofuran-4-carboxylic acid, 5-(4,6-dimethoxypyrimidin-2-yl)oxy-3-ethylthiocarbonyl-2-methylbenzofuran-4-carboxylic acid, and pivaloyloxymethyl 5-(4,6-dimethoxypyrimidin-2-yl)oxy-3-propoxycarbonyl-2-methylbenzofuran-4-carboxylate.
 19. A condensed heterocyclic derivative of the formula (I): ##STR523## wherein: A is a heterocyclic ring of the formula ##STR524## R is a hydrogen atom; a hydroxyl group; an alkoxy group which may be substituted with pentanoyloxy, butanoyloxy, hexanoyloxy, ethoxycarbonyl, ethoxy, ethylmalonyl, benzoyloxy, (2'-trimethylsilyl)ethyl, methoxy, trimethylsilyl or (2'-methoxy)ethoxy; a benzyloxy group which may be substituted with methoxy; a phenyloxy group; a C₁ -C₂ alkylthio group; a benzylthio group; a phenylthio group; a C₃ -alkenyloxy group which may be substituted with Br; a C₃ -alkynyloxy group; a C₃ -alkenylthio group; a C₃ -alkynylthio group; a C₃ -alkylideneaminoxy group; O⁻ [N(CH₂ CH₂ CH₂ CH₃)₄ ]⁺ ; O⁻ (CH₃)₂ CHNH₃ ⁺ ; O⁻ CH₃ CH₂ CH₂ NH₃ ⁺ ; O⁻ Na⁺ ; or a group of the formula --NR⁶ R⁷, whereineach of R⁶ and R⁷, which may be the same or different, is a hydrogen atom, a C₁ -C₄ alkyl group, a benzyl group, a phenyl group, a methylsulfonyl group or a phenylsulfonyl group; or R⁶ and R⁷ may, together with the nitrogen atom, form a 1,3-imidazole ring, pyrrolidine ring, piperidine ring or morpholine ring; each of R¹ and R², which may be the same or different, is a hydrogen atom; a formyl group; a C₁ -C₈ alkylcarbonyl group which may be substituted with fluorine; a cyclopentylcarbonyl group; a benzoyl group which may be substituted with chlorine; a pyridylcarbonyl group which may be substituted with methylsulfonyl; a carboxyl group; a group of the formula --CONR⁶ R⁷ ; a C₁ -C₈ alkylthiocarbonyl group which may be substituted with diethylamino; a C₃ -C₈ cycloalkylthiocarbonyl group; a phenyloxycarbonyl group which may be substituted with chlorine or methoxy; a C₁ -C₈ alkoxycarbonyl group which may be substituted with fluorine, chlorine, bromine, 2-furyl, 2-thienyl, cyano, ethoxycarbonyl, hydroxy, dimethylamino, cyclopropyl, methoxy, ethoxy or methlythio; a C₃ -cycloalkyl group; a C₁ -C₈ alkyl group which may be substituted with fluorine, chlorine, methoxy, nitro, cyano, methoxycarbonyl, dimethylamino or hydroxy; a C₂ -C₃ alkenyl group which may be substituted with CN or nitro; a C₃ alkynyl group; an ethoxy group; a methoxy group; a phenyl group which may be substituted with chlorine; a halogen atom; a benzyloxycarbonyl group which may be substituted with methoxy; a benzylthiocarbonyl group; a C₃ -C₈ cycloalkoxycarbonyl group; a phenylthiocarbonyl group; a C₃ -C₆ alkenyloxycarbonyl group which may be substituted with chlorine; a C₃ -C₆ alkynyloxycarbonyl group; a C₃ -C₆ alkenylthiocarbonyl group; a C₃ -C₆ alkynylthiocarbonyl group; an isopropylideneaminoxycarbonyl group; a nitro group; a cyano group; a halogenated carbonyl group; a group of the formula CR⁸ ═N--R⁹ ; a group of the formula NR¹⁰ R¹¹ or a group of the formula N═CR¹² R¹³, wherein:R⁶ and R⁷ are as defined above; R⁸ is a hydrogen atom, a phenyl group, or a methyl group; R⁹ is a hydroxyl group, a propyl group, a phenyl group, a benzyl group, a benzyloxy group, a methoxy group, a propoxy group, a propenyloxy group, a propynyloxy group, a phenoxy group, a methylamino group, a dimethylamino group, a phenylamino group or a phenylsulfonylamino group which may be substituted with methyl; each of R¹⁰ and R¹¹, which may be the same or different, is a hydrogen atom, a methyl group, a phenyl group, a benzyl group, a formyl group, an acetyl group, a benzoyl group, a pyridylcarbonyl group, an ethoxycarbonyl group, a methylsulfonyl group, a phenylsulfonyl group, a carbamoyl group, an ethylthiocarbonyl group or a phenylthiocarbonyl group which may be substituted with chlorine, or R¹⁰ and R¹¹ may, together with the nitrogen atom, form a morpholine ring; and each of R¹² and R¹³, which may be the same or different, is a hydrogen atom, a methyl group or a phenyl group, or R¹² and R¹³ may, together with the carbon atom to which they are bound, form a cyclopentylidene group; each of R³ and R⁴, which maybe the same or different, is a hydrogen atom; a methoxy group which may be substituted with fluorine; a halogen atom; a methylamino group; a dimethylamino group or a C₁ -C₆ alkyl group; Y is a halogen atom, a methyl group, a methoxy group, a phenyl group, a nitro group, a methylamino group or a dimethylamino group, n is an integer of from 0 to 2, provided that when n is 2, it may represent a combination of different groups, W is an oxygen atom, a sulfur atom, an N-formyl group, a methylene group, a carbonyl group, a cyanomethylene group, and Z is a methine group;or a salt thereof.
 20. The condensed heterocyclic derivative of claim 19, wherein:one of R¹ and R² is a hydrogen atom; a formyl group; a C₁ -C₈ alkylcarbonyl group which may be substituted with fluorine; a cyclopentylcarbonyl group; a benzoyl group which may be substituted with chlorine; a pyridylcarbonyl group which may be substituted with methylsulfonyl; a carboxyl group; a group of the formula --CONR⁶ R⁷ ; a C₁ -C₈ alkylthiocarbonyl group which may be substituted with diethylamino; a C₃ -C₈ cycloalkylthiocarbonyl group; a phenyloxycarbonyl group which may be substituted with chlorine or methoxy; a C₁ -C₈ alkoxycarbonyl group which may be substituted with fluorine, chlorine, bromine, 2-furyl, 2-thienyl, cyano, ethoxycarbonyl, hydroxy, dimethylamino, cyclopropyl, methoxy, ethoxy or methlythio; a C₃ -cycloalkyl group; a C₁ -C₈ alkyl group which may be substituted with fluorine, chlorine, methoxy, nitro, cyano, methoxycarbonyl, dimethylamino or hydroxy; a C₂ -C₃ alkenyl group which may be substituted with CN or nitro; a C₃ alkynyl group; an ethoxy group; a methoxy group; a phenyl group which may be substituted with chlorine; a halogen atom; a benzyloxycarbonyl group which may be substituted with methoxy; a benzylthiocarbonyl group; a C₃ -C₈ cycloalkoxycarbonyl group; a phenylthiocarbonyl group; a C₃ -C₆ alkenyloxycarbonyl group which may be substituted with chlorine; a C₃ -C₆ alkynyloxycarbonyl group; a C₃ -C₆ alkenylthiocarbonyl group; a C₃ -C₆ alkynylthiocarbonyl group; an isopropylideneaminoxycarbonyl group; a nitro group; a cyano group; a halogenated carbonyl group; a group of the formula CR⁸ ═N--R⁹ ; a group of the formula NR¹⁰ R¹¹ or a group of the formula N═CR¹² R¹³ ; and the other of R¹ and R² is a C₁ -C₈ alkylcarbonyl group which may be substituted with fluorine; a cyclopentylcarbonyl group; a benzoyl group which may be substituted with chlorine; a pyridylcarbonyl group which may be substituted with methylsulfonyl; a carboxyl group; a group of the formula --CONR⁶ R⁷ ; a C₁ -C₈ alkylthiocarbonyl group which may be substituted with diethylamino; a C₃ -C₈ cycloalkylthiocarbonyl group; a phenyloxycarbonyl group which may be substituted with chlorine or methoxy; a C₁ -C₈ alkoxycarbonyl group which may be substituted with fluorine, chlorine, bromine, 2-furyl, 2-thienyl, cyano, ethoxycarbonyl, hydroxy, dimethylamino, cyclopropyl, methoxy, ethoxy or methlythio; a benzyloxycarbonyl group which may be substituted with methoxy; a benzylthiocarbonyl group; a C₃ -C₈ cycloalkoxycarbonyl group; a phenylthiocarbonyl group; a C₃ -C₆ alkenyloxycarbonyl group which may be substituted with chlorine; a C₃ -C₆ alkynyloxycarbonyl group; a C₃ -C₆ alkenylthiocarbonyl group; a C₃ -C₆ alkynylthiocarbonyl group; an isopropylideneaminoxycarbonyl group; a cyano group; a halogenated carbonyl group; a group of the formula CR⁸ ═N--R⁹ ; a group of the formula NR¹⁰ R¹¹ or a group of the formula N═CR¹² R¹³.
 21. An herbicidal composition containing an herbicidally effective amount of the pyrimidine derivative of claim 20 and a carrier therefor.
 22. A pyrimidine derivative or a salt thereof according to claim 17, wherein each of R³ and R⁴ is an alkoxy group having 1 to 6 carbon atoms.
 23. The condensed heterocyclic derivative of claim 19, wherein:R¹ is a C₁ -C₈ alkyl group which may be substituted with fluorine, chlorine, methoxy, nitro, cyano, methoxycarbonyl, dimethylamino or hydroxy; an ethoxy group; or a methoxy group; and R² is a hydrogen atom; a C₁ -C₈ alkylcarbonyl group which may be substituted with fluorine; a C₁ -C₈ alkyl group which may be substituted with fluorine, chlorine, methoxy, nitro, cyano, methoxycarbonyl, dimethylamino or hydroxy; or a cyano group.
 24. A condensed heterocyclic derivative of the formula (I): ##STR525## wherein: A is a heterocyclic ring of the formula ##STR526## R is a hydrogen atom; a hydroxyl group; an alkoxy group which may be substituted with pentanoyloxy, butanoyloxy, hexanoyloxy, ethoxycarbonyl, ethoxy, ethylmalonyl, benzoyloxy, (2'-trimethylsilyl)ethyl, methoxy, trimethylsilyl or (2'-methoxy)ethoxy; a benzyloxy group which may be substituted with methoxy; a phenyloxy group; a C₁ -C₂ alkylthio group; a benzylthio group; a phenylthio group; a C₃ -alkenyloxy group which may be substituted with Br; a C₃ -alkynyloxy group; a C₃ -alkenylthio group; a C₃ -alkynylthio group; a C₃ -alkylideneaminoxy group; O⁻ [N(CH₂ CH₂ CH₂ CH₃)₄ ]⁺ ; O⁻ (CH₃)₂ CHNH₃ ⁺ ; O⁻ CH₃ CH₂ CH₂ NH₃ ⁺ ; O⁻ Na⁺ ; or a group of the formula --NR⁶ R⁷, wherein:each of R⁶ and R⁷, which may be the same or different, is a hydrogen atom, a C₁ -C₄ alkyl group, a benzyl group, a phenyl group, a methylsulfonyl group or a phenylsulfonyl group; or R⁶ and R⁷ may, together with the nitrogen atom, form a 1,3-imidazole ring, pyrrolidine ring, piperidine ring or morpholine ring; each of X¹ and X², which may be the same or different, is an oxygen atom, a sulfur atom, a methylene group, a carbonyl group, a group of the formula NR¹⁴, a group of the formula C═NOR¹⁵ or a hydroxymethylene group, wherein:R¹⁴ is a hydrogen atom or a methyl group, R¹⁵ is a methyl group, and when one of X¹ and X² is an oxygen atom, the other is a sulfur atom or a group of the formula NR¹⁴, Q¹ is a methylene group, a carbonyl group or a group of the formula C═C<R¹⁶ R¹⁷, wherein:each of R¹⁶ and R¹⁷ which may be the same or different, is a cyano group, a cyclopropylcarbonyl group, a benzoyl group or a methoxycarbonyl group; and if Q¹ is a methylene group, then X¹ is a methylene group and X² is a carbonyl group, a group of the formula C═NOR¹⁵ or a hydroxymethylene group; Y is a halogen atom, a methyl group, a methoxy group, a phenyl group, a nitro group, a methylamino group or a dimethylamino group, n is an integer of from 0 to 2, provided that when n is 2, it may represent a combination of different groups, W is an oxygen atom, a sulfur atom, an N-formyl group, a methylene group, a carbonyl group, a cyanomethylene group, and Z is a methine group;or a salt thereof.
 25. An herbicidal composition containing an herbicidally effective amount of the pyrimidine derivative of claim 10 and a carrier therefor.
 26. An herbicidal composition containing an herbicidally effective amount of the pyrimidine derivative of claim 12 and a carrier therefor.
 27. An herbicidal composition containing an herbicidally effective amount of the pyrimidine derivative of claim 16 and a carrier therefor.
 28. A pyrimidine derivative or a salt thereof according to claim 16, wherein each of R³ and R⁴ is an alkoxy group having 1 to 6 carbons.
 29. A pyrimidine derivative or a salt thereof according to claim 12, wherein A in the formula (I) is (A-12).
 30. A pyrimidine derivative or a salt thereof according to claim 12, wherein A in the formula (I) is (A-12), W is an oxygen atom or a sulfur atom, and each of R³ and R⁴ is an alkoxy group having 1 to 6 carbon atoms. 